Chapter Sixty Two

As she drove Jon home, her phone, which was connected to the car for music and GPS, had been blowing up with messages from Brady. She kept having to swipe them off the dashboard screen so Jon wouldn’t see Brady’s name pop up. When Jon had gotten out of the car, she was finally able to check her texts. It was mostly a bunch of drunken gibberish, but Brady had made it clear that he hoped she would come over.

She thought about it, wondering if she really wanted to hook up with a drunk guy when she was stone cold sober. Whiskey Dick is definitely a real thing, so she wondered if it was even worth her time. The deciding factor, though, was his insistence on how good he was with his tongue. At the very least, if he couldn’t perform, she’d still be able to get hers, so she agreed to go meet up with him.

She texted Brady that she was on her way, and then input his address to her GPS. Coincidentally, he lived literally 5 minutes away from Jon. Very convenient, actually. She headed over there and texted him when she arrived. He was still in an Uber on his way home. It was about 10 minutes before a black car with tinted windows pulled up. She then saw this sharply dressed, albeit stumbly, red headed man emerge from the backseat. He had on a beige peacoat that he buttoned up as he walked towards his house. Very classy, even though he was drunk and a little bit messy.

She got out of her car and walked up to meet him. He smiled and greeted her with open arms. Damn, he was so hot. They walked up his front stoop and briefly recounted their evenings as he unlocked the front door. Even in his drunken state, he was charming and funny and just the right amount of pervy. Cheeky, even. Whatever he was, he turned her on and she was happy she had gone over.

His house was like a tri-level type thing. The main entrance was on the lower level, and you had to walk up a set of stairs to get to the kitchen and living room. It was a really nice house. They walked upstairs and in to the kitchen. She leaned back against the island and he offered her a beer. As she opened it and took a sip, he stepped in real close, his face hovering closely above hers. As he gazed down at her with a sexy stare, he slipped his hand into her shirt and kissed her. They made out a bit as he felt her up, then she started rubbing him outside his jeans. It felt like he was up to the challenge, but as she unzipped him, she realized that nope, he definitely was not.

And while we’re on the subject, she was actually kind of happy he couldn’t fully get it up. This was not a particularly attractive penis she was looking at, not that any of them are, really. But she had never seen such a skinny dick before! Small, sure. But his wasn’t particularly small or short, just incredibly, incredibly skinny. Like, have you ever heard the term “needle dick”? It’s very crass, of course, but for the first time in her life, she understood what that meant. What a disappointment! It was then, though, that he lifted her chin and tilted her head up to look him in the eyes. “Can I lick you now?” he asked. Ah, the silver lining.

They hurried up the next flight of stairs and headed to the bedroom. “Get naked” he ordered her. Mmm, yes sir! She lay down on the bed and he crawled on top of her. They started making out again, his hand moving down her body as he started to pleasure her. Soon, he moved his way down, and began to work those tongue skills he had been raving about.

It was good, for a bit. But eventually he was just completely missing the mark. She actually started to get a little bored. He must have sensed that she wasn’t in to it, because it was then that he paused and opened his night stand drawer. Low and behold, a magic wand vibrator.

Now, let’s be clear. Did she want to use a sex toy that she knew for certain had been used on other women? No she did not. But! Was she so sexually frustrated at that point, knowing he wouldn’t be getting her off, and knowing that she wouldn’t be able to go home and use her own vibrator because her parents were home/it was like four in morning at that time? Yes. The answer is yes.

All she wanted to do was finish what he had started. She made sure the vibrator was clean, then just did her thing. He loved it and enjoyed watching her. As soon as she was done, she jumped up and ran in to his en suite, closing the door behind her. She grabbed the hand soap and lathered herself up, making sure she was as clean as she could be, before coming back out. The idea of having shared a sex toy with who knows how many other women, just made her feel… blech.

When she opened the door, he was laying in the bed welcoming her in for a cuddle. She threw her tank top on and joined him, but at that point it was just awkward. The moment had definitely passed, so she got herself dressed and Brady followed her out, still completely naked.

Even after he had failed to please her, he was still putting on the charm. He flirted with her as she zipped up her boots, his skinny little wiener just danglin’ away. Brady kissed her goodbye as she opened the door and left. She got in her car and looked at the time; 4:30am. “What a waste!” she thought to herself. When she got home, she smoked a joint in the garage and headed up to bed as quietly as she could. Despite the disappointing ending, everything before that was great, and she had still had a super fun night.

The next morning she woke up to two texts from Brady, making sure she had enjoyed herself. She didn’t want to shame his shitty tongue skills or thin equipment, so she said she had a fun time, but suggested that if it did happen again, that they both be sober. Then she took a shower.

Surprisingly, Brady stayed in contact. He’d reply to her Instagram stories, or send her dirty pics here and there. His junk looked much bigger in pictures. She enjoyed the attention and found that they kind of became just like, flirty Instagram buddies. He’d ask her what her weekend plans were, she’d tell him and ask him the same. Often they’d each have dates with other people, and would end up wishing the other luck. It was during those conversations that he’d confessed to her how much he enjoyed “sloppy seconds,” as he put it.

Turns out Brady was pretty freaky. He got off on having a girl sleep with someone else, then go over to his place and he’d have sex with her again. He liked it even more if the guy had finished inside the girl, and then he’d get to eat her out afterwards.

Told ya. Freaky.

In the nearly two years of her being single, she had learned that everyone has their thing. So, even weird stuff like that didn’t necessarily scare her away. If she could handle Chad the Foot Fetishist, she could handle Brady wanting her to fuck other guys. In fact, the more he talked about it, the sexier it sounded. Maybe not the part about finishing inside her and him eating some other guys.. stuff.. out of her (😬). But the idea of her having sex with someone, and Brady wanting her so badly afterwards he has to fuck her too? That was kind of hot. At the very least, she entertained the idea of it over text.

Soon, December had arrived and society was doing it’s best to focus on Christmas, rather than the world falling to pieces. Early that month, she and her friends had arranged to have a Friendsmas gettogether. One of her friends and her fiancé had graciously offered to host, and had even gone as far as organizing a Murder Mystery Christmas dinner. Everyone had their own characters to play, and it was such a creative and unique way to spend the evening. She and her friends hadn’t all been together in a long time, so everyone really enjoyed themselves.

Later in the evening, after they had eaten dinner and the murderer had been unmasked, they were all just sitting together in the living room drinking and enjoying each other’s company. She checked her phone and saw an Instagram notification. She thought it was just someone liking the pic she had posted of herself in character, (Kitty Killer: journalist, biographer, spy… not a cat killer), but it was actually a message from Jon.

He was, in fact, complimenting the photo, but he also messaged just to catch up and see what she was up to. Obviously he realized she was busy, but he told her that she was welcome to stop by afterwards. At this point she was already a bottle of wine deep, so the thought of hooking up after a fun night with her friends was too tempting to pass up.

It was after 2am when she and her friend, and her friends husband who was DD, had finally left. She got a ride to their place, then called a cab to drive her the rest of the way to Jon’s house. She texted him when she arrived, and he came out front to meet her…

Continue to Chapter Sixty Three

Chapter Sixty One

One morning, a little while later, she was at work, tapping away on her computer, when she saw her phone light up. It was a notification from Facebook Dating. She ignored it until her lunch break, but when she went to check it, she was very pleasantly surprised by who had Liked her.

We all know of her affection for gingers, even though they’ve proven to her time and time again that they’re toxic and not at all good for her. “Who cares!” she thought. This guy was so hot! He had reddish-blonde hair, a well coifed ginger beard, and good eyebrows (which is hard to find with gingers). She matched with him immediately.

She sorted through the other notifications she had, then went to grab her lunch. When she got back to her desk she had a message from Ginger Boy. We’ll call him Brady. Brady went hard right away, telling her how sexy she was and asking what she was doing at that moment. She replied that she was at work, and asked what he was up to. He responded by admitting he’d taken a break from working from home and was currently having a bunch of dirty conversations with a few girls on the app.

Yes, she saw the red flag. Yes, she ignored it.

If anything, she was more intrigued than before. She didn’t know this guy, for all she knew this could have been the one and only conversation she’d ever have with him. She approached it as if she were just chatting with a friend. As a supportive cheerleader, even. Her lack of repulsion to his honesty seemed to pique his interest in her more, as well, and they began a back and forth of sexual hypotheticals. Great. Now she was horny at work.

Their conversation continued throughout her lunch break, and he continued to message her throughout the afternoon. She ignored the notifications as much as she could, but her curiosity and love for attention were often too much to bare. She got very little work done that day.

They chatted throughout the evening, and off and on over the next couple of weeks. He kept asking when she’d be over to fuck him, and she kept responding that she’d be down to meet for coffee or a drink, and then see where things went from there. He was not receptive to coffee, and kind of evasive in regard to the drink. He was only interested in the hook up.

Yes, she saw those red flags. Yes, she ignored them too.

Even though they weren’t in lockdown at the time, pandemic life left few opportunities to really go out on the town. Finally, one Friday night, out of sheer luck and coincidence, she and her friend were able to follow through on their plans to actually go out for drinks.

Seeing as it was November, it was cold out, and she did not live close to where they had intended to go. So, instead of paying for a cab and having to bare the elements on her journey to the bar, she decided to take one for the team and be DD. She’d have a drink or two, but that would be it. She really just wanted to enjoy the atmosphere of a bar, more than she wanted to get drunk. She missed the noise, the people watching, the chance to meet a cute guy… She knew she’d have fun no matter what, so she picked her friend up and off they went.

Being in their mid-thirties, she and her friend arrived at the bar before 9pm, and honestly, they had never been so grateful for their age. Within half an hour of their arrival, the bar went from Dining to Bar Service, which meant no more table service, no more walk-ins, bouncer stationed at the door and a line up down the street. Phew! Dodged that bullet!

Now it was a party. The music got louder, some tables were moved out of the way, and as people left or got up to mingle, she and her friend were able to score a way better table than where they had been seated, and were now occupying prime people watching real estate.

Earlier that day she had been chatting with Brady, and he had asked what her plans were. She told him she’d be going out, and he said he was too. Neither of them told the other where they were going, but both agreed to message each other later and see where they’d end up. Her friend was a genius and had ordered them each a second drink before their server was cut. As they finished their first drinks, her friend popped out for a smoke.

As she sat alone at the table awaiting her friends’ return, she scrolled though Instagram and sipped her beer. It was then she saw Brady’s story, and noted that he was at a bar just a few streets over. “Interesting…”, she thought to herself. As she continued to sit there alone, the urge to message him grew stronger and stronger. Finally she couldn’t resist it any longer and sent him a quick, “how’s your night going?” Her friend was back shortly, though, so she closed her phone and they resumed their fun.

She had been nursing her beer for a good hour, while her friend had gone through nearly 2 more. (She was only a teensy bit jealous) The bar had filled up with seemingly every vaccinated person in the city, and she and her friend were having a great time. “Come out for a smoke with me!” her friend begged. “Yea, no.” she replied. She wasn’t a smoker, so there was no way she was about to A) stand out in the cold to watch her friend smoke a cigarette, or B) lose their awesome table! She was fine to sit alone for a few minutes every now and again.

“You’re drunk and brave,” she told her friend. “Go find us some guys to flirt with!” Her friend delivered. After about 10 minutes, she came back in with two guys she had met outside. “I made some friends!” her friend announced as she scooched back into the booth, followed by two guys who were clearly much younger. “You’ll never guess,” her friend began. “These guys went to the same high school as us!” “No way!” she exclaimed. That was actually pretty cool, yet also not super surprising because their big city often seemed like a very small town. Everyone knows everyone.

“When did you graduate?” she asked the guy who had chosen her side of the booth. “2012,” he replied. Ooof! Way to hit her where it hurts! She had graduated in 2005, just to put things in perspective. “How old are you??” she asked. “26,” he smirked. “Oh! That’s my cut off!” she laughed. After Kyle, she had told herself that 26 was the youngest she’d ever consider. “Oh, well lucky me,” the guy replied. “It was my birthday a few weeks ago…” Oh man… made it in just under the wire. “What’s your name?” she asked him. “Jon” he replied.

Jon was tall and thin, with a mild “Guido” vibe to him. The sides of his head were shaved, and the rest of his hair slicked back. Sounds like a greasy, slime ball type guy, but this look worked for him, somehow. He had nice brown eyes, light scruff, great teeth, and a deep, silky voice. She introduced herself as well, and they began a surprisingly interesting conversation.

Jon was actually quite the intellectual. He was well versed in politics, pop culture, music of all genres and periods, and even art! It was so rare that she was able to have an in-depth conversation about art with a guy, or anyone really. She was enthralled by him, when all of a sudden she looked up at a guy walking past their table.

Who was it, you ask? Why, Chad, of course! The foot fetish guy! The guy who had humiliated her and sent her spiraling. (See Chapters 41 – 44)

She immediately looked across the table at her friend, who was chatting away with Jon’s buddy. Her friend noticed her looking at her, and she tried to whisper to her that she had just seen Chad. “WHO??” her friend drunkenly shouted, having not heard her over the vibrations of the crowd partying around them. “Never mind, I’ll tell you later” she laughed. Jon was curious about what she was trying to tell her friend, but she brushed it off and changed the subject, all the while, keeping an eye out for where Chad had gone. Not because she wanted to talk to him or anything, but to ensure that he wasn’t anywhere near her.

She got back into the conversation with Jon, while her friend went and got them some more drinks. As she and Jon chatted, she continued her people watching. It was then that she realized that Chad was hitting on some girls at a high-top directly behind her booth. Wtf man! Go away! She turned her back to him and carried on her conversation. Despite Chad’s lingering presence, she really was having fun.

Some time passed, and she eventually had to pee. This bar was one that didn’t have any big bathrooms with stalls. The bathrooms were scattered throughout the bar, all individual. She lucked out and found an empty one near their table. She went in, did her thing, was only in there for a few minutes, and when she opened the door… Chad was standing front and centre. Like, she opened the door and they were literally face to face.

She had never seen blood rush out of someone’s face faster than Chad’s as he realized who she was (which is saying a lot considering Chad is basically a ghost). His smile dropped and his eyes bulged. She was less shocked than he was because she had already seen him, but she was still surprised to see him up close and personal as she came out of the bathroom! They stood there for what felt like an eternity but was honestly like a split second, before she did an awkward swimming-like hand gesture indicating for Chad and his friend to step aside so she could squeeze through. Fuckin’ small-town-big-cities…

Jon saw her returning and graciously stood up to let her back into the booth. At that point she didn’t care anymore and she told the whole table what had just happened to her. She also pulled no punches giving details about Chad’s foot obsession. Fuck that guy! They all laughed and made fun of him. It was great. (To be clear, there’s no fetish shaming here. The shame is specifically directed at Chad. But also, heads up to any guys reading this, women don’t want you to fuck them with your foot. They just don’t. It’s not hot. It does nothing for us. But if a woman does agree to it, you better treat her like the god damn sexually-generous queen she is! But I digress…)

The night rolled on. Her friend and their new, young pals got good and drunk, and it was about that time to be headin’ on home. She checked her phone and saw several drunk texts from Brady, a few of which were messages asking her to go over, along with his address. She laughed and replied that she’d be leaving soon, and she’d text him later.

During her conversation with Jon about how they went to the same high school (8 years apart), they had discovered that they lived in the same end of town. Therefore, she insisted on driving Jon home rather than him taking an Uber. He asked if she was sure about 100 times, before gratefully thanking her for saving him $40.

The bar had cleared out a bit, and as they gathered their things to leave, she caught a glimpse of Chad, seemingly sober, sitting in a booth with some sloppy drunk woman at least 10 years older than she was. Clearly all the young, hot babes had blown him off, and he was settling for whatever he could get. “I hope that drunken cougar throws up on you…” she thought to herself as they headed out.

She, her friend, and Jon walked the like 7 blocks to where she had parked (she was not a great downtown driver), and headed home. She dropped her friend off first (which was not a strategic move, it’s just geography), then headed over to Jon’s house.

Jon lived off a street that she had driven down, oh, maybe a million and one times. Seriously, it’s crazy the coincidences that kept coming up that night. She parked the car and they both agreed that it was really nice to have met one another. She hadn’t expected to kiss him, but he gave her the eyes and the lean in, so she leaned in too and they had a hot li’l makeout sesh. “Do you want to come in?” he asked. “Aw, I’d love to,” she replied. “But I have to be up early tomorrow. Another time though!”

She did not, in fact, have to be up early the next day. She did, however, have plans to go over to Brady’s…

Continue to Chapter Sixty Two

Reflecting on 2021

2021… What can I say?

For the world, this past year was just an extension of the shit show that was 2020. For me, it was a year of sexual awakening.

By summer, most of us were all vaccinated and real life opened up for us again. I was able to go out for patio drinks with friends, I took a road trip, I went camping. I even flew out to BC to visit family. Getting back to “normal” was such a blessing, but it also allowed me to slip back in to old habits that haven’t really served me.

Reflecting on this past year and re-reading some of the chapters I’ve posted, I’ve realized (not like I didn’t already know) that I’m a bit boy-crazy. It’s like I live and breathe for the chance to hook up. After all the growth and progress I gained through 2020, I feel now, like I let that slip away a bit, and I fell back into the endless search for that dopamine rush I feel when I have a guy’s undivided attention, if only for a limited time.

I’ve also discovered that boredom is my enemy. The pandemic has made boredom an almost everyday occurrence. It’s when I’m bored that I seem to seek out male attention, making me feel static and vibrant and out of my self. I feel like I’m living in a world inside my head where it’s just me and whichever guy I’ve chosen to chat with online. But I’m not chatting with these guys about dating and what I want from a real relationship. It’s always only about sex. These conversations with strangers, which start off so innocently, always take a dirty left turn. At the guy’s behest, I end up going in to detail about the sexual things I enjoy, and vise versa.

The constant over-sexualized image of myself that I’m putting out has finally got me wondering; why is that the version of myself that I’m making so prominent? And though I’m not a psychologist, it’s got me wondering if this is all still a trauma response from my toxic relationship?

It’s been almost two years since I ended the relationship that led to all of this. My ex was verbally, mentally and emotionally abusive. He was also a sex and porn addict. He was on his phone day and night looking at naked girls on Tumblr, or just full-on watching porn as we sat next to each other on the couch. His obsession obviously made its way into our bedroom. He would always want me to do these crazy sexual positions, would be showing me images of scantily clad or fully naked women, comparing me to them. Asking me why I can’t look like that? Or why I wouldn’t do X, Y, or Z sexual positions?

His obsession became mine, but in the opposite way. I became so prudish and sexually reserved. I had no libido. I hated sex and everything to do with it, especially porn. I resented it. Not that I just love it now or anything, but at least I’m no longer consumed by anger towards it. His sex obsession even made me avoid self pleasure. I felt disgust and shame at the thought of it. Anything to do with sex, I made off limits for me. It was my way of shielding myself from the humiliation I felt for not looking like those women on Tumblr or in pornos. Shielding myself from how much I hated how I looked and that I was never enough to please him, so why try? I would never be like those women. I wasn’t sexy enough or pretty enough or skinny enough or desirable enough.. whatever it was. I retreated from anything sexual and really didn’t enjoy sex for almost a decade, the entirety of my relationship.

But now, there’s been this sexual revolution inside me. I’ve done a lot of self healing and have worked hard on my mental health. I’ve learned how worthy I am of every kind of love, including sexual. But, having yet to find someone to give me the romantic love I desire, I’ve settled in to this sexual limbo of meaningless hook ups and never-ending bad dates. I feel like I’ve become obsessed with sex in the same way my ex was. Am I over compensating for the time I lost in that loveless, sexless relationship? Am I oversexualizing myself because that’s what I’ve been brainwashed to think is the only way one could be viewed as desirable? My dopamine levels sky rocket when a guy tells me how sexy I am or how much he wants to fuck me. I live for that shit… which really can’t be healthy.

I’m realizing that these endless hookups are just limiting my chances of actually finding a meaningful relationship. That being said, until recently, I really wasn’t interested in a meaningful relationship. I was genuinely enjoying these random hook ups. I guess I *was* making up for lost time.

It wasn’t completely bad. I felt(feel) powerful in my sexuality. I’ve enjoyed discovering my sexual self. I’ve learned so much, and I don’t think I realized until recently, how freaky I actually am. Again though, these newly discovered sexual interests could very well be influenced by the unhealthy ideas ingrained in me from my ex. But by taking my sex life in to my own hands, I was able to discover pleasure in it, rather than shame.

Even still, it’s begun to feel empty. One random hook up after another. The original goal was to find a Friend with Benefits so I wouldn’t be out there fucking a bunch of random strangers, but FWB’s are really just pre-boyfriends, I’ve discovered. There’s still a sense of commitment expected in a FWB relationship, and most guys still can’t handle that.

This realization has led me to believe that I don’t just want to hook up with random guys anymore. I guess I’m finally ready to settle down with someone again. There’s still a part of me, though, that’s afraid of being hurt. But now also, I worry about craving the dopamine rush from the attention I get from other guys.

Not that I condone cheating by any means, but having all these guys on the go and not being committed to any of them, has given me a glimpse in to why people might cheat. The validation you get from attention like that can be overwhelming and, sometimes, even all consuming. I worry about settling down with someone but still craving that outside attention. But then I guess, if I find someone who checks all my boxes, I won’t be craving that external validation. Which then brings me back to the fear I have of getting hurt again. All these meaningless hookups check one box, sexual pleasure and attention, but then I don’t risk my heart breaking or someone actually getting close to me for real.

All of that to say, I need to re-focus. Not that I’ve completely gotten off track. Even through all these dating and sexual mis-adventures, I’ve still been able to maintain my goals of getting myself healthy. My eating habits might need some re-calibration again, but I’m proud to say that I’ve been consistently working out for a whole year. Over a year, in fact.

My body has changed so much in the last 13 months. I’ve lost weight and gained muscle, clarity, and self worth. Working out has given me not only physical strength, but mental strength as well. It’s kept me sane and driven throughout this entire Covid nightmare. I’ve been able to steady my anxiety by keeping focused on exercise. It’s barely allowed me time to fret about the decline of human civilization as we know it. And I know myself; I could very easily have spiraled in to an abyss of fear and worry. But I didn’t. And that’s something else I’m proud of.

By working out consistently, I’ve learned that I am strong; much stronger than I ever would have thought. I’ve learned that I truly can do anything I set my mind to. Anyone who knew me in my younger days, even before my ex, is probably just as surprised as I am to see me looking the way I do now. Oh and might I add, my doctor is thrilled! She showed me a linear graph of my weight over the years. It looks like data from Wall Street. Like the stocks are going up, up, up, then all of a sudden they plummet. That was my weight loss.

But so, if I know I’m capable of putting myself first and making my mental and physical health a priority, now it’s time to make my romantic life a priority too. The only way to do that, though, is to not make it a priority, know what I mean? I have to focus my attention on the things that I *can* control: my health, my happiness, and my finances. By letting my libido run the show, I haven’t been able to stick to my goal of getting my finances in order. The chance to go out and party always took priority over saving money to put towards my future. YOLO, right? But now I’ve done that. I’ve partied. I’ve gone out. And because of that, I’m *still* living in my parents’ guest room.

Last year my goal was to buy myself a car, which I did. I’ve owned cars before, but this is the first time I was able to buy (finance) one on my own. And not even a used car. I bought a brand new (at the time) 2021 sedan. On my own. Me! I’m still so proud of myself for that. It’s given me the freedom to live my life and rediscover all the things that bring me joy. But last year I also manifested that I would have moved out by the spring. This goal did not come to fruition.

Therefore, for 2022, I’m re-manifesting that this will be the year I finally become fully independent and move out on my own once again. Then I’ll have everything that a young(ish), independent woman would need. And hopefully, once all aspects of my life have fallen in to place, I will finally have room in my heart to welcome a true romantic partner.

That being said, I don’t know what this blog will look like in the future if I’m truly going to start limiting my dating life. I do have a few more stories to post in the new year, but I really hope I’m able to shift my priorities to what really matters. I hope the same for all of you. Hard to do as we teeter near the start of year 3 of this god damn pandemic. But the only way to get through it all is to keep focused on your goals, surround yourself with likeminded people, and stay safe.

Wishing everyone peace, joy, and lots of sex in the new year! May 2022 bring you everything you could ever need xo

Stay tuned for more chapters in the new year, Wednesdays at 8pm, EST.

Chapter Sixty

She and Whistler Man chatted for hours the night they matched. We need a better name for him… Jason. Let’s call him Jason.

She and Jason chatted for hours the night they matched. He was funny and charming and showered her with compliments. It was a Tuesday night, so they arranged to meet up for a date that coming Friday.

She had started her new job the day they connected. She was still struggling with her decision to change careers and was feeling a lot of stress and anxiety. So when Friday rolled around, she really wasn’t in a social mood. The thought of making small talk and, once again, briefing some new guy on her traumatic dating history was the last thing she wanted to do. However, when he texted her about it, she was reminded of the connection she felt towards him, even if it had only been via text, so she decided not to bail.

Luckily, his family lived in her end of town so they were able to meet up at a little pub close to her house. She arrived before him and was sat a high top in the bar. It’s so awkward being the first one to arrive for a date. Do you get up and hug when they arrive? Do you wave them down if they don’t see you? If they’re running late, you just sit there like a loser for however long it takes them to arrive. So annoying. Fortunately, she was just a tad early, and he was right on time.

Their eyes met from across the crowded restaurant. Shew knew he was tall, but she didn’t realize how tall. He must have been 6’5, minimum. “Yaasss!” she thought to herself. He had his mask on, but she could see his gloriously thick and well kept beard peeking out. He wore a flat beak skater hat, a zip-up hoodie, and a pair of jeans. His “fancy jeans”, he would mention later on. In all fairness, he didn’t pack for dating, he packed for family relaxation. His style definitely screamed, Man/Boy, but she reminded herself that he was a snowboard instructor in Whistler. How else would she have expected him to dress?

He approached the table and sat down quickly. Phew! No awkward hug. They both stared at each other, giggling awkwardly. She didn’t know why she was so nervous! It’s not like this was her first date since her ex or anything. Maybe his nervousness was rubbing off on her? Whatever it was, the longer their stared and sat awkwardly, the more the sexual tension mounted between them. They had had some racy conversations over that past week, and it seemed they didn’t even need to speak for that chemistry to boil up inside them.

The server came over and they ordered some drinks. That seemed to break the tension a bit. He asked her about her job, her family, her life post-breakup. She asked him about his passion for snowboarding, his life out in Whistler, and his family whom he came to visit. Once they got to chatting, the conversation flowed like water. She was so comfortable and he was so easy to talk to. They compared dating war stories, he told her about the crazy surgeries he’s had to have due to snowboarding injuries, and she told him about how she chipped her tooth at that exact restaurant when she was drunk one time. Same, same.

Their drinks came and they ordered food. The food wasn’t great, but the conversation still was. Once they were done eating, they decided they would walk over to a little pot shop around the corner. They split the bill (which she wasn’t used to, but also wasn’t offended by), and headed over to buy some weed.

Unfortunately, it was 11:05pm when they arrived, and the dispensary closed at 11pm. They stood out front for a few moments, figuring out what to do. As they decided, she just stood there shivering. It was then, with his hands in the pockets of his sweater, he opened his arms wide and offered to keep her warm. She cuddled up to him and he just enveloped her up in his hoodie, his arms wrapped tightly around her. She just melted in to him. There are few things in this world that can top being hugged by a tall, warm, sweet guy in a hoodie. It was one of the best hugs she’d had in recent memory.

It was then that she looked up at him, the top of her head barely reaching arm pit level. He was gazing down at her, that look in his eye. You all know the look 😏… He leaned down, she reached up, and they kissed. It was sweet and soft at first, but the passion grew the longer they stood there lip locked. Their make out sesh was paused as they heard the bell of the nearby pizzeria door open. They both turned as a pizza guy walk out.

She looked, and did a double take. What are the friggin chances?! Not only did this pizza guy happen to be someone she had matched with on Hinge many months prior, this particular guy was actually someone she had gone to high school with! He looked over as he walked out the door, and there really was no getting around it, he definitely saw and recognized her. She was hard to miss with her blue hair. She turned and hid her face in Jason’s chest, and through muffled laughs told him that they had to leave there, post haste!

They walked around the corner, now holding hands, and he invited her to come back to his place. By his place, he meant his parent’s place. No judgement, obviously. She still lived with her parents (lived with her parents again, rather), and he was just visiting. Who was she to say anything? Still, parents are not typically conducive to a sexy good time.

“They’ll be sleeping,” he said as he tried to convince her. She weighed her options, and was actually leaning more towards just going home, but then he hooked her in with the promise of a massage. After all the stress she was dealing with in regards to her job, she actually really did need one. So she agreed. He had taken a cab to the restaurant, so they headed over to her car and she drove them back to his place.

They snuck in quietly, the sound of the TV blaring from the basement. Jason told her to run upstairs, as he went down to investigate. She scurried up to his bedroom, sitting awkwardly on the corner of his bed. A few moments later, he walked in and closed the door. His parents were still awake watching a movie, so no funny business could be had. Instead, he set up his laptop to watch a movie, and he crawled in behind her on the bed, positioning himself to give her the massage he had promised.

They agreed to watch The Addams Family (Halloween was the next day, after all). He rubbed her shoulders and her neck as they watched Wednesday Addams try to behead her younger brother (That’s true romance, right there). But as his hands went back and forth in very PG areas of her body, slowly, they moved their way down. Soon, she was leaning back against him as he felt her up over her shirt. She could feel his excitement in the small of her back. The tension just kept growing and growing. They both wanted to just rip each other’s clothes off, but couldn’t risk getting caught by his parents. Eventually, though, his hands moved further south, and he began undoing the button of her jeans. Unzipping the zipper. Slowly reaching his hand down when –

KNOCK! KNOCK! KNOCK! “Jason? Are you up?” his dad’s voice rang in from behind the door. “I’m sleeping, dad. Goodnight!” Jason, the 40 year old man, shouted back (😆).

They froze there for a few moments. His one hand on her boob, the other lingering just outside her jeans. They heard his dad’s footsteps head back downstairs, and it was in that moment that they just couldn’t hold back any longer. Within seconds, he flipped her around, both their shirts came off, and they began a crazy intense make out sesh.

He rubbed her outside of her jeans, she did the same. Soon his pants her off, hers on but fully unzipped now. She sat on top of him, straddling him, grinding slowly. Without her saying anything, he reached up and started choking her gently, but with just enough force that she felt her entire body tingle. She wanted nothing more than for him to rip her clothes off and just take her. But they couldn’t. They just kept teasing each other, the sexual tension building and building. Fuck. It was so hot.

Eventually, there was nothing more they could do in the situation they were in. They tried to just cuddle for a while, but they always ended up fooling around again. Around 2am, she decided she had to go. Jason was still in town for a while so they agreed to get together again. It just so happened, his parents were heading up to their cottage the next day. However, the next day was Halloween and she already had plans to go to her friend’s Halloween party. She invited Jason to come, but he opted not to. So they agreed that she would just go over to his place afterwards.

She thought about him the entire next day. He texted her to come over earlier, but she had a bunch of stuff to do before the party, and had also promised her friend that she would go over early to help decorate. The anticipation just made things even hotter.

Night fell and the party was in full swing. It wasn’t a huge turn out considering they were still smack dead in the middle of Covid, but it was a fun time nonetheless. This group of friends happens to be really in to the rave scene, and they love all that EDM music. Definitely not her cup of tea, but she always tried not to be a Debbie Downer. It wasn’t until whichever DJ came on the playlist who played really bass heavy type stuff that she finally had to say something. She had been drinking, obviously, but was also able to get her hands on some shrooms, no thanks to Kyle. But maybe this wasn’t the best place to do that, after all? The bass was heavy and it felt like it was penetrating her soul. The other party goers graciously changed the music when they realized how fucked up she felt, but even still, she just felt like she was on a different level than the rest of her friends. She texted Jason and told him she was leaving the party early (if 1am is early?).

Surprisingly, the cab arrived in no time, and she was on her way. Dressed as a School Girl, short, pink, plaid skirt and a white, midriff bearing tie-up top, she hauled her giant duffle bag with all her clothes and Halloween costume supplies and headed over to his place. He was waiting for her at the end of the driveway when she arrived. She drunkenly stumbled out of the cab, lugging her duffle bag behind her. He chivalrously took it from her and carried it inside.

As soon as the front door closed, they were all over each other. He had her up against the wall, leaning on the stairs, and they even, somehow, ended up on the kitchen floor. She was fucked up but she was definitely aware enough to know this was fucking hot. They moved the party upstairs and just ravaged each other. Kyle was still the best sex she’d ever had, but she remembered thinking that Jason was definitely a close second. She loved a guy who could anticipate her desires and embrace her freaky side without her having to say it.

Eventually they had exhausted each other and needed a well deserved break. They cuddled and talked, not that she could remember the conversation, and after a little while they went down to the basement to watch a movie. He poured them each a glass of wine (oh yea, like she needed that…), and they put on The Addams Family Values (because, of course!). He sat on the couch and she cuddled up to him, laying her head in his lap. Not sexually, believe it or not. However, as they watched the movie and she inevitably readjusted herself, he began touching her all over again. Teasing her, revving her up and then slowing down. It was torture. The best kind.

They fooled around like that for a while until they noticed the movie had finished. It was about 5am at this point and they both agreed it was time for her to go home. She called a cab and they waited together in the kitchen, watching for her ride from the kitchen window. As they waited, they, again, just couldn’t keep their hands off each other. Neither of them could get enough. Unfortunately, the cab didn’t take very long. They shared a long, deep, passionate kiss and they said their goodbyes. She got in the cab and watched Jason watch her drive away. It wasn’t until that moment that she was truly disappointed that he didn’t live there.

They messaged a bit the next day, but their conversation dwindled throughout the rest of the week that he was still there visiting. He had told her which day he was going home, so she texted him to have a safe flight, but didn’t get a reply. It wasn’t until a few days later that he responded. He was still the same sweet, funny, charismatic guy she had connected with, and she was happy to not get ghosted again. Even now, they still text here and there, or he’ll comment on her Instagram stories. For now, that was enough for her. But she was definitely looking forward to him visiting again… even if it’s not until next year.

Continue to Chapter Sixty One

Chapter Fifty Nine

She and Kyle continued texting and messaging here and there, and she confirmed the date of the Halloween party with him. She even sent him a funny text about a conversation she had been having with her co-workers about period sex, saying that she told her co-workers about the first time she and Kyle had hooked up and what a champ he was (see Chapter 49). She praised him for being so good in bed. He laughed and replied, “I’m glad you’re enjoying yourself. My pleasure 😘” and invited her over after work. She wasn’t able to go because she had a staff meeting that night, but man oh man, she wished she could have.

The week before Thanksgiving, she messaged Kyle about their hike. “Heyyy… Still down for a hike on Monday? Followed by some super hot sex?? 😏” (Don’t worry everyone, she knows how smooth that was..) She sent that text on her lunch break, but got no reply. “Okay,” she thought. “He’s working too. He’ll reply later” But he never did.

The next day, she saw an Instagram story he posted about a Covid outbreak at a festival he had attended the weekend before. She kicked herself for thinking that he was ignoring her. “He’s sick with fucking Covid, you bitch!” she told herself as she picked up her phone and sent him another text to see how he was feeling.

She waited until the next day, he still never replied. “He better be dying of Covid and not just ghosting me…” she angrily thought to herself. And no she didn’t actually mean it that she hoped he was dying of Covid. She was just trying to rationalize with herself that he was sick and there had to be an actual reason for him not to reply to her texts all of a sudden.

But there wasn’t. He was full on ghosting her. Randomly, out of no where. He just up and decided he was done talking to her and that he would ignore any texts he received from her, presumably hoping that she’d take the hint. Which, of course, she did.

She understood quickly that she was being ignored. Which obviously put her into a mini spiral of insecurity. She wondered what she had done to trigger this disappearance. It was the hike, wasn’t it? She knew it was too big a step for this friends with benefits relationship.

After that short bout of self doubt, she snapped back to reality and realized that it was nothing she had done that had caused him to ignore her. Whatever the reason was, it was a him problem. She had told him many, many times during their cuddle sessions that she was happy with their casual relationship. She didn’t want anything more from him. She didn’t want a full commitment, she didn’t want all his time and attention, and she especially didn’t want him to meet her parents or her friends (the ones he hadn’t met yet, anyways).

And even going hiking, that wasn’t an attempt to start something more with him. She really just wanted a chance to build up some sexual tension before going back to his place to fuck! She wanted to flirt with him and tease him and make him want her but not be able to have her because they were out in public. Come on, people, that’s hot! It would have been fun to take their sexual chemistry out of the four walls of his bedroom.

And if he didn’t want to go, he could have just said so. Why agree at all if you’re not going to follow through? It was Thanksgiving, for fucks sake! He had a built in excuse right there. Even if it was a lie, she couldn’t have argued with that and she wouldn’t have brought it up again. (Not that she would had argued if he had said no, regardless of the reason. He would have been completely entitled to just not want to go, and she would had respected that either way.)

And even if he had wanted to go originally but changed his mind, why ghost her? She figured after all the time they had spent together, he would have had enough decency and respect for her to at least fucking tell her, “Hey listen, I’m actually not really feeling it anymore. I’m really sorry, I know I said I would. Another time, maybe…” Easy as that.

Would it have sucked to have gotten that text? Well obviously. Of course she would have been disappointed. But at least she wouldn’t have felt tossed aside and disrespected like she did when he just ignored her instead. Wasn’t he trying to work on himself? Become more mindful? Working towards becoming a better, more whole person? How does ghosting someone achieve any of that??

It was a full two weeks that she hadn’t heard anything from him. Halloween was approaching and, aside from inviting him to the party, she had also asked Kyle to see if he could get her some ‘shrooms for the occasion. She had only done them a handful of times before, but thought it might be fun to do on Halloween. She used that as an excuse to make one last ditch effort to get him to talk to her.

“Hi. Sorry to text you again. I don’t know if you’re sick from that festival or just busy or whatever, but I was just wondering if you’re still coming to Halloween? Last time I was over we talked about you helping me get some shrooms for that night. If you’re still able to, that would be awesome. If not, I’ll figure something else out. Let me know” She resisted truly giving him shit. At the very least, she hoped she could still get those shrooms out of him. But again, no reply…

Until the next evening.

“Hey, sorry if I’ve been MIA for a while. Wasn’t the right thing to do so I apologize for that. But no, I won’t be able to go to the Halloween party. I got a new job where I work on weekends now so I won’t be able to stay up late. I’m still sick from the festival but I’m feeling good now. My shroom guy is super sick, probably has Covid, so I’ll have to wait to get some stuff from him”

She contemplated not replying. Why should she? And what would he care either way if she did or didn’t? Ultimately, she did reply. It’s not in her to ignore people. Must just be that she’s a better person than him, that’s all (😆) All she said was, “Kk. Glad you’re feeling better. Good luck with the job .” (If he even did have a new job? Who knows..)

Some time later, she was on Instagram and must have searched him, realizing that she hadn’t seen a story by him in a while. When she looked at his profile she discovered that, not only had he been ghosting her, he had hidden his stories from her as well. Whyy?

Why did he all of a sudden just like, full on hate her? Was he perhaps seeing someone new? Okay, fine. But just tell her! What was it with guys just dropping people so casually like it doesn’t even matter? She was especially frustrated by this hurtful act because she had just been in this exact situation herself, with Greg. She wasn’t in to him, but she felt like the decent thing to do was to break the news to him in a kind but clear way. And here Kyle was, not even giving her that same courtesy.

She knew what their relationship was. She was almost a decade older than Kyle. Of course if he were to get in to a real relationship with someone it would be with someone his own age. She knew that whenever she got into a real relationship, it wouldn’t be with him either. Ideally it will be with someone her own age or older. But if that happened while she was still seeing Kyle, she damn well would have told him about it and not ghosted him and blocked him on Stories.

So that was it. That was the end of her interactions with Kyle. Yes he was in his 20’s and immature and just a dumb guy and all the other things one can tell themselves in situations like this. But what it came down to was that he was a nice guy who made her feel good, who appreciated her body and her sexuality, and who really hurt her feelings by just ignoring her like that without so much as an explanation. It sucked. But it is what it is, right? Moving on, yet again.

Fortunately, around this time, all the chaos with her job had been occupying her mind and she didn’t have a lot of time to sit around and dwell on this failed FWB situation. She was working hard to sort her shit out and if Kyle didn’t fit in with this new life she was building for herself, then fuck it, it’s better that it ended, then. In the meantime, though, she was obviously still cruising the dating apps. She chatted with guys here and there, but none of them sparked her intrigue enough to keep the conversation going. Then one night, she randomly matched with guy on Hinge.

Hinge was (and probably still is) her least favourite of the dating apps. She didn’t like that you have to use the prompts they give you instead of just writing up a little blurb about herself. She also found that most of the guys on there were looking for more serious relationships, and that still wasn’t exactly where she wanted to be yet. However, one night she got a notification that someone had liked her on the app.

She checked and saw this tall, kind of goofy looking yet ruggedly handsome guy with a killer beard, had sent her a rose. She wasn’t sure if she wanted to match with him because his photos weren’t really all that great, but something inside her told her that this poor guy just wasn’t very photogenic, and to give him a chance.

She matched with him and he sent her a message pretty quickly. They got to chatting and soon she discovered that he was originally from her end of town, but that he had moved out to Whistler many years ago and was just back for a family visit. “Perfect” she thought. After the whole Kyle thing, she didn’t want to get involved with someone on a somewhat regular basis again. On the other hand, having someone fawn over her and give her the attention she craved, at least for a little while, could be exactly what she needed…

Continue to Chapter Sixty

Chapter Fifty Eight

Greg continued to message her throughout the entire next week. She replied here and there with very generic responses because she still wasn’t sure how she would let this guy down gently. She didn’t want to ghost him, but she thought it might be a tad hurtful to just flat out say, “Your insecurities, small dick, and weird home life are all huge turn offs for me. Sorry, pal. Peace out!”

One evening, after he messaged her but she had told him she was busy, he replied asking if she would text him the next day. It was then she decided that she couldn’t drag this out any longer. She sat down and wrote out a draft text before sending him anything.

She wrote that he seemed like a very genuine, kind, caring person – exactly what she would have been looking for if she were looking to settle down. She said that she knew he wasn’t looking for something serious at the moment, but she could still sense that he was more eager about their interactions than she was. She empathized with his sad home life and understood that he was mainly just looking for sex, but explained that there was just too much attached to that considering what he was going through with his (ex)wife. She told him that she had her own issues to deal with and that she didn’t have room in her life to take on someone else’s baggage, even just casually. (Look at those boundaries! OoOOohh someone’s growing 😉) She wished him happiness and told him that she hoped he’d be able to move on from the situation his was in.

He responded almost instantly. “Hey. No worries, I totally understand. It was really great meeting you. All the best.”

Phew!! What a relief! She was happy she hadn’t let the one sided texting go on too long, and was proud of herself for setting boundaries, while still remaining kind towards Greg. The last thing she wanted to do was hurt his feelings, even if she had zero interest in him. She knew giving him closure would be kinder than ghosting him.

Saturday came around, and she was looking forward to relaxing after a long week of text avoidance. She had worked out in the morning, and was now stoned, munching on some Smartfood and watching Netflix. Her phone lit up, and she glanced down at it, assuming it was just an IG notification, but it was actually a text. She almost threw her bag of popcorn when she saw Kyle’s name. Her grubby, cheese covered fingers grabbed her phone and opened it so she could read his message.

“Hey you! Was wondering if you were free tomorrow during the afternoon for some fun. Let me know 😘”

Wasn’t much notice, but it was better than a same day sex request. She waited a few minutes before responding, but she had literally zero chill about it. “Oooh, yes please” she replied. “What time?”

“2pm. Bring your toy 😉”

Yaasss!! After the whole Greg debacle, she was due for some really good sex.

She drove out to Kyle’s place the next afternoon, and texted him when she was there. He asked her to wait a few minutes, presumably so he could tidy up quickly, then he told her to walk in. She opened the door and he greeted her at the front entrance. She barely had her shoes off before he grabbed her by the scruff of her neck and kissed her deep and hard. She dropped her purse and let it spill open on the floor as he pushed her up against the wall and they started tearing off each other’s clothes.

They made out there for a while. Deep, hard, passionate kissing. She had missed it more than she realized. He just always instinctively knew what she liked and how she liked it. She was half naked by the time they decided to move it to the bedroom.

They both got undressed and he pushed her onto the bed. She lay on her back and he spread her legs as he knelt down between them. Wow, wow, wow. God dammit he’s good at that. He pleasured her for as long as it took to get her off twice, before climbing on top of her. They tossed themselves around that bed for hours, enjoying each others bodies and making each other feel amazing. Her entire body felt like jell-o by the time they collapsed into each other’s arms to rest.

This was one of her favourite parts of their trysts; when Kyle would wrap his big, muscular arms around her and they would just lay with each other, their bodies intertwined, as they came out of the fog of that blissful, post coital haze. It was then that they had their most intimate conversations.

Since they hadn’t seen each other in a while, they had some catching up to do. She filled him in on her job and her friends, mentioning that she was hoping to get out for a hike with them sometime soon as it was early Fall and the leaves were almost at their peak. He told her that he loved hiking, then filled her in on what he had been up to in his life, as well. He confided in her that he had actually been doing a lot of self reflection. He was working on becoming more mindful, especially in regards to his fear of romantic commitment.

He also explained why he hadn’t reached out to her in recent weeks. In his efforts to be more self aware, he had decided to really give it a try to be committed to his girlfriend-not-girlfriend. He said that he had tried to be monogamous with her, knowing that that’s what she wanted and that he wanted to make her happy. But ultimately, it just wasn’t for him. He felt too restrained, unable to be himself, even just in casual conversation with female friends. In the end, he decided it would be better to end the relationship.

She thanked him for confiding in her with all that. She praised him and told him how proud she was of him for trying to be more emotionally mature – a rarity for his gender in general. She told him she was happy for him that he was working on himself, and that she was happy to be hanging out with him again.

She left a little while later but had some errands to run quickly before going home. As she was driving, she got a text from Kyle. Siri read it out to her, “Let me know when you get home safe, gorgeous” Damn, okurrr, she thought to herslef. (She didn’t actually think that. Not once in her life, until this very moment, had she ever said “okurrr”. It just fit so appropriately in that sentence). She was used to him texting her to hook up, she wasn’t used to him, or any guy really, being thoughtful like that.

She texted him when she got home and thanked him for all the fun they had had. She told him she hadn’t felt pleasure like that in a while, to which he replied, “Good. You deserve it baby, I got you 😘” Ugghh. That sentence alone was almost enough to get her off again.

The next day was Monday. She came home from work and reluctantly completed another workout in her self-imposed Make It To Thanksgiving Workout Challenge. She always posted a pic of herself on IG after a workout. It helped her hold herself accountable, and she enjoyed visually tracking her progress. So, she posted her pic and carried on about her evening. Later, she saw that Kyle had sent her a little fire emoji, which of course made her feel good. But he then went on and said, “I wanted to tell you that you looked great, btw. I could see your progress when I was on top of you 😘”

She felt butterflies explode throughout her entire body. She had been working so hard on herself over the last year and a half, it was truly an overwhelmingly uplifting moment to have someone comment on her progress like that. She thanked him, and told him that he made her feel both vulnerable and flattered at the same time. He was sort of confused by that and worried that he had insulted her, but she explained that it was a good thing. For someone who had seen the absolute most intimate side of her to compliment her like that, especially when she wasn’t expecting it, it just made her blush, that’s all.

They texted each other and messaged each other on Instagram off and on over the next little while. Sending memes and commenting on each other’s stories. She invited him to a Halloween party that her friend (whom he knew) was having, and he accepted. He also invited her over a couple more times during the preceding weeks, but the timing just didn’t work out. But finally, one random Thursday evening, she was able to go over to his place after work.

Again, it was another earth shatteringly pleasurable experience at Chez Kyle. They exhausted each other over several hours, and when they had finished, they decided to actually Netflix and chill. They were having a hard time agreeing on something, when he suggested they watch Squid Game. It had just come out and he was dying to watch before all the spoilers hit the internet. They cuddled together and turned it on, but before long they were both sitting up, reading the subtitles and being shocked by one thing after the next. They only watched the first episode before she decided it was time to go home. It was getting late for a work night, and she still had a half hour drive ahead of her.

As she was gathering her things they chatted casually about this or that, and she mentioned again that she and her friends were having a hard time finalizing a date to go hiking. She was hoping to go on Thanksgiving Monday since she knew no one would be working, but so far none of her friends had been available. Then, surprisingly, Kyle replied that he might be down to go hiking with her instead.

“For real?” she asked, incredulously. He laughed and nodded yes. “But like, for real for real? On Thanksgiving? You’ll actually come hiking with me?” “Yes!” He said. “Sounds like fun.” She couldn’t believe her ears. Yes, she TOTALLY had been hinting at it and was hoping he would take the bait, but she definitely didn’t expect that he’d actually want to go for a hike with her.

“Okay…” she began. “But you can’t bail then. If you actually want to go hiking with me, then we really, truly, have to go. Don’t say yes and then not come…” She had experienced it too many times, a guy saying he wanted to do something and then flaking. “I’m not!” he insisted. “Text me about it later, but yes I’m down.”

She couldn’t contain her joy and definitely did a little happy dance. She kissed him and wrapped her arms around his neck. “Okay great, I’ll text you later this week…”

She finished putting on her shoes and headed out. She was already imagining them hiking through the woods, admiring all the gorgeous fall colours, then going back to his place to have super hot sex. She also knew, though, that this was a bit of a big step in whatever their relationship was. They had never actually gone on a “date”, if that’s even what this hike would be? As excited as she was, she never quite fully believed that he would follow through. “We’ll see…”, she thought to herself.

Continue to Chapter Fifty Nine

From Diapers to Desktops…

Let me pose a question to you; Do you work at your dream job? A profession you’ve loved since you were young, that fills your heart and soul with joy? A place that you actually enjoy going to every day?… I do. Well, I did. And okay, maybe it wasn’t my DREAM job, but it was my life for a long time, and I was damn good at it.

When I was 16 years old, I was at Christmas dinner with my extended family and my cousin’s wife happened to mention that she worked in childcare. She was an educator at a Montessori daycare. Did I know what Montessori was at the time? Definitely not. But she had me at “daycare”.

As you all likely remember, in high school, when you hit Grade 12, you better damn well know what you want to do with the rest of your life! I, like all of you (probably), had no idea. But when my cousin’s wife was talking to me, it was like a lightbulb went on in my head. I had always loved children and at the time, aside from also working at Tim Hortons, I made most of my money through babysitting. Why had it never occurred to me to look in to childcare as a career?

After heeding my family’s advice, I applied to the Early Childhood Education program at my local college. I was accepted, and I spent the next two years in school learning the basic skills needed to work in daycare, as well as completed three placements. I graduated and immediately began working as a supply teacher at one of the centres I had been placed in during my schooling. I continued on to university, while maintaining my supply teacher status and working in daycares when I was able.

After my university graduation, I took some time to re-think my life goals. I had just graduated with a bachelor’s degree in Art History. In the three years post college, I studied subjects that had absolutely nothing to do with children. Did I really want to work with kids for the rest of my life? I had rekindled my childhood passion for art and swore I would work at an art gallery, or at least in the field of art… Turns out, that life proved more difficult to obtain than I had originally thought.

When the art thing didn’t work out, I fell back on my first passion. I was fortunate enough to be hired at the daycare my brother and younger cousins had attended when we were children. It was a crazy time warp to be back there as an adult, but I fell in love with the field of childcare again and I knew I had made the right choice. I believe strongly in signs, so I was receptive when it became clear that the Universe had other plans. The art thing just wasn’t in the cards for me (though it is still a huge passion of mine), and I know for a fact that I was meant to work with kids.

I worked at that daycare for three years. Were they the best years of my life? Absolutely not. I worked in both the preschool room, and the toddler room. The children were some of the cutest, funniest, sweetest beings I had ever come in contact with. They lit up my days with their smiles and their laughter. I absolutely loved being there for those kids.

The owner/Director of this centre, however, was a tyrant. She ran that place like a sweat shop and refused to compensate her staff accordingly. I was unceremoniously fired from that job because I spoke up for myself against another teacher. A teacher who happened to be best friends with the owner. Nepotism, much? I contacted the labour board and, fortunately, they found that I had been unlawfully terminated, and I was therefore compensated with EI until I found my next job.

At the time, I was still with my (ex)boyfriend. He had just been accepted to college in a little town about an hour and a half north-west of where we were living. Getting fired was actually perfect because it allowed me time to pack up our place and go look for new apartments in our new town. We found a place, and I began applying at every daycare I could find. The problem was that none of these daycares were offering the same wages as the big city paycheques I was used to. Let’s be clear though, teachers and educators make shit money regardless, but in this small town, the pay rates were much lower than I had been receiving.

Still, I eventually found a job at a military daycare one town over from where I had just moved to. Only about a 15-minute drive, not too bad. I was hired to work the Before and After School program for the Jr. and Sr. Kindergarteners. It was a split-shift, though. So not only was I making less money, but I also had to both open and close the centre. At the time, however, none of that mattered to me. I was just happy to be working at a centre that valued my skills and ambition in this field. I felt so supported and encouraged by the Director of this centre, and I made so many friends there. Many of the educators at that first daycare were snotty bitches. Yes, I made some friends, whom I’m still in contact with today, but over all it was a very toxic work environment.

Not at this new centre, though. At this place, it really felt like everyone was on the same team. Everyone just wanted to provide the best care possible for these children. Children who were already learning the hardships of life at such young ages by having to deal with and understand why their parents were gone away (ie: military deployments). Aside from the one parent left at home, we as educators were some of the only constant sources of comfort and care for these children. I took that responsibility very seriously. The bonds I made with those kids have stuck with me, even years later. I like to think they feel the same way, but I know they’ve all probably forgotten me by now. Still, I know I played a crucial role in their lives and I do no regret the shitty pay cheque one bit.

I worked at that daycare for another three years before my then-boyfriend got a job about 6 hours north from where we were living. Aside from the shitty pay and shitty hours, I could have worked at that daycare forever. I loved my co-workers, I loved my boss, I loved those kids. Money doesn’t always buy happiness, y’know?… But yes, it helps.

After moving up north, it was difficult to find a job. I was hired at a daycare attached to a catholic school. Didn’t work there long, though. Our philosophies on discipline and care differed greatly, let’s just put it that way. A few months later, however, I was hired at the cutest little hippie daycare I ever did see!

This place was fantastic! The owner/Director was very much in to a naturopathic lifestyle. Everything there was as organic and natural as possible. Even the food colouring was organic – it was made from vegetables!! (Note to anyone looking to use natural food colouring: be sure to put it in the fridge when you’re not using it. I found this out the hard way once I discovered mouldy food colouring jars in my supply cabinet [insert puke emoji here]).

Not only did this daycare centre align with my own lifestyle and beliefs, but the pay was much higher than what I had been making before. The staff were a close-knit group which was hard to crack, but once I did, those ladies showed me nothing but kindness, appreciation, respect and friendship. I was so happy to have found an amazing work environment that paid well.

The downside was that it was another split shift, this time with the older School Age kids. School Age is my least favourite age. They’re old enough to talk back and be shit heads, and there’s pretty much nothing you can do about it. The pro to this new job though was that when I wasn’t working with the big kids, I was covering breaks for teachers in other programs. I was still able to get my baby and toddler cuddles in, so I took it as a win.

I worked there for a whopping 7 months. I had finally had enough of my horrible, toxic, abusive relationship, so once I broke up with my boyfriend, I had to quit my job and move back home to live with my parents. That was the end of January 2020.

Through serendipitous connections, I was able to land a job at another daycare within two weeks of returning home. This time, I would be working with Infants. FINALLY! My favourite age group! I was so excited! My first day was February 16th 2020. Just shy of a month later, we closed for Covid.

Fortunately, we were only closed for three months. When we opened again, it was limited numbers. If I recall correctly, we were only offering care for parents who were essential workers. I had two babies in my program at the time. Eventually, as the pandemic progressed, so did our safety protocols. Our class size limits went up and soon we had full numbers again. Once we were at capacity, obviously the other staff were brought back also.

For the most part, the staff at this centre welcomed me with open arms. Specifically, my room partner. Let’s call her Maggie. Maggie is 10 years and 4 days younger than me. We’re both Cancers, and I truly have never felt so connected to another person like that, maybe in my whole life. We were so in sync! Whatever I thought, she thought. Whatever task I had in my head to do next, she would be doing it by the time I got around to it. We could read each other’s minds, it felt like. We disciplined the same way, we executed our programming the same way, our philosophies on work and life and just, everything, were all the same! The Infant program ran like clockwork because of our exceptional team work. Never in my entire life had I clicked with a co-worker as easily as I had clicked with Maggie.

We became friends outside of work too. We partied together, we got each other Christmas and birthday gifts and just… ugh. She was more than just my coworker. She was one of my closest friends. Like a sister.

A year and a half in to the pandemic, a lot had changed around the centre. We had gotten a new Director, whom we all adored, but then she went and got knocked up with twins and was left to go on maternity leave several months early. Even before she left for early mat-leave, I had spoken with her privately asking who would be lined up to replace her. She wasn’t sure, but she said she’d pass along my inquiry to the owners. I asked about it several more times, each time with no information to be given.

By this point, it had been 14 years since I started in this field. I had worked all over the province, worked with every age group possible, I had more experience than many staff at the centre. I felt like I was at the top of my game, and even though I was being paid well for a daycare teacher, it still wasn’t enough. Since moving home less than two years ago, I’ve blown myself away with how much I’ve accomplished. However, financial independence still seemed unattainable in my current position. Did I want the Director position? Not really. But did I want the money and the perks that came with it? You bet your ass I did.

This past August, I went away on a family trip to BC – first big trip since the pandemic hit. I was so excited. While I was away, I received a message from one of the admin’s at the centre saying that my Director had to go on maternity leave early, and asked if I was available for a Zoom interview the next day. The original interview time would have been impossible to coordinate based on the time difference between provinces, so I arranged for it to be a bit later. The problem was that I was going to be flying in to Vancouver from Victoria after having visited a friend for a few days. I literally landed at the airport and had to run to find a quiet place I could do this zoom interview with both of the owners of the daycare.

I barely recall what was asked or what was said during that half hour. I was so frazzled from the urgency of getting off the plane and doing this unexpected interview that I was sure I botched the whole thing. Still, I was asked to do another interview later that day. This time I was in the privacy of my aunt’s bedroom and felt a little bit more at ease. I thought it all went well, but I was on vacation. So after I hung up, I let it fade from my mind until I got home two days later. The more I thought about it, the more certain I was that I was going to get the job.

The Sunday before I went back to work, I received a phone call from one of the owners. “Unfortunately, we’ve decided to go with someone else,” she said. My heart sank and my stomach tied in knots. Through the golf ball sized lump that was forming in my throat, I managed to blurt out, “Oh, okay. Who are you going with?” There was a pause, and then she replied, “Maggie.” It felt like my entire body was lit on fire. The rage I felt seemed to burn through my skin.

“May I ask,” I replied as calmly as possible. “What was the deciding factor? What did she have that I didn’t?” The owner hmm’d and haah’d on the other end before saying, “Oh well, you were both great. But we felt it was important that our next Director be fluently bilingual. We’ve never had a bilingual Director and we think it would be beneficial to the centre.”

I couldn’t even think straight. I don’t know how the conversation ended but I knew that all I wanted to do was throw my phone and smash the shit out of something. Are you fucking kidding me?! Bilingual!? THAT’S the reason my years of experience mean absolutely fuck all to you people?! Hey! Guess what! JE PARLE FRANÇAIS AUSSI!!! It was never once mentioned that being bilingual was an asset. I have been busting my ass in this field for years! And Maggie gets a promotion over me, after only working in the field for barely two years, simply because she’s bilingual?!

FFuuuccckkk yyyooouuuuu!!!!!

Even writing all this, I want to smash my fucking laptop. It’s bringing back all those feelings of shock and rage. And now I was just expected to go in to work the next day like everything was hunky-dory?! Well, guess what! That’s exactly what I did because I am a god damn professional! I even sent Maggie a congratulations text after I got off the phone with the owner.

I went in to work the next day to find my other room partner there, as well as a supply teacher. You know, to cover for Maggie who was now my fucking boss, apparently?? I don’t even know how I made it through that week. I was literally a shell of the person I normally am. Honestly, I think I was in actual shock. Like true, traumatic shock. I had put all my eggs in to that basket. This was going to be it for me. Finally, after so many years of shitty shifts and shitty pay, I was finally going to get promoted and put all my experience in to making this daycare centre the best it could possible be… But now what?

What do I do now? Keep working in the same position for the same pay as if nothing happened? As if I had no pride or dignity? What person with any ounce of self respect could keep working in that job after that? But what, I’m going to quit and go work for some other shitty daycare for worse pay? No, definitely couldn’t do that. For the moment, I just had to bend over and take it.

As the days went by, however, I was able to process my feelings and direct my anger towards the appropriate target. Was it Maggie’s fault that they chose her instead of me? Absolutely not. All the qualities and skills that Maggie possesses, the things that made her the ideal room partner, were all the reasons she had been chosen for this job. She is smart, and feisty, and adaptable. She’s got a great sense of humour but she takes no shit. She’s organized and professional. She’s polite but stern. She possesses all the qualities that would make her an ideal candidate for this job. As an “older sister”, I’m proud of her. That’s not to say, however, that I don’t still feel like I could have done it, too.

Fortunately, I had been able to contain my true feelings fairly well. Well enough that Maggie knew I was upset, but that I was also a grown ass professional woman who wouldn’t bring her personal feelings in to the workplace in a disruptive manner. One morning, during her first week as Director, I was able to steal a quiet moment with Maggie before the centre opened. I explained that my problem was not with her. I told her I was happy for her, and that I hoped it wouldn’t affect our friendship. We hugged, and cried a little, and I left that interaction feeling lighter than I had that whole week. Still though, I knew I had to find a new job.

I immediately began applying to government positions. I sent my resumé to anyone I know who worked for the government. My friend’s fiancé even helped me update my resumé to be more office directed, as opposed to just all daycare work. How would I pull this off, though? I have almost zero administrative experience. Unless you count the one month I worked at Statefarm Insurance?

Years and years ago, I had gotten hired at Statefarm during my time off from childcare. I heard about the position through a family friend. The insurance agent seemed to be in a real pinch and was looking for literally anyone to fill the receptionist position. Turns out the former receptionist had been involved with the insurance salesman in the office. She was married, however, and unsurprisingly her husband didn’t take too kindly to this relationship. There may or may not have been a big brawl at the office, after which the receptionist quit and moved home to the UK.

I was hired to answer phones and write up insurance quotes. “No experience necessary,” the agent said. Turns out, YES experience necessary! I had absolutely no idea what I was doing! I was there just under a month before he realized he didn’t have time to babysit me and walk me through every step of my job. Nor did he have anyone who could train me. And so ended my short career in office work.

Several weeks passed as I waited to hear back from the government positions I had applied to. In the meantime, it was clear that the owners of the daycare knew that they were on rocky ground in terms of me staying. They knew how valuable I was for the Infant program, and the centre in general, so they offered me some bullshit, made-up position where I would basically be a stand-in for some administrative positions. When other admin staff were unable to be there or do something for whatever reason, then I would step in and cover for them. Only on those occasions would I get a raise. Otherwise I would still be working my normal position for my normal rate of pay.

Of course, I graciously accepted this non-existent position. How could I turn down the potential to make more money? I figured, until I hear back from one of these other jobs, I’ll let the owners think things are fine. It was about a month after that, however, that an opportunity was presented to me that I simply couldn’t refuse.

All my life, my mother and my aunt have worked in the field of subsidized housing. So when a position became available at my aunt’s office, she sent me the link. She made it clear that that was the extent of her involvement in this process. She knew I was competent enough to get the job on my own, and didn’t want to risk anyone thinking there was any nepotism involved with me potentially getting hired. I applied, and within a few days, I heard back that I had been selected for an interview. I did the interview via Zoom while sitting in my car in the parking lot across the street from the daycare. It was a Thursday, and I was officially offered the position the following Monday.

I couldn’t believe it. I was both ecstatic and terrified at the same time. There had been several times throughout the decade+ that I had worked in childcare when I had considered leaving the field. The bullshit I experienced at this most recent centre was certainly not exclusive to this one daycare. As you’ve read, there was bullshit with every centre I worked at – bad pay, shitty co-workers, bad bosses… But regardless, I always chose to stay.

It takes a very special person to work with children. I am definitely that kind of person. I love almost everything there is to do with working in daycare. I love being creative and planning all sorts of fun crafts and activities to do with the kids. I love playing and being silly with them, I love being a source of comfort for them when needed. The bonds I had made with these dozens and dozens of children over the years had always meant so much to me. Not only that, I loved that I knew I was good at it.

If you’ve read this much of the blog you’ll know, I’ve always had serious insecurity and self esteem issues. But never, not once, did I ever doubt my talent and skill for this job. The kids loved me, my programming was always top notch, I often mentored other educators who were new to the field, or worked collaboratively with other experienced educators to create amazing activities for these tiny humans. This job was my passion, my life. The bullshit that came with it always sucked, but the job itself… I just loved it.

But now I was presented with this new opportunity. This giant fork in the road of my life. Which path do I take? Do I stay with what I know and love, but continue to be taken advantage of and unappreciated? Or do I take the risk of trying something new? What if I suck at this new job? What if I hate working in an office? All these “what if’s” sailed through my mind, but all I kept telling myself was, “you’re better than this place.” And I am. I deserve to be appreciated, to have my skills and experience recognized and valued. I deserve to be praised for my efforts, not taken advantage of because I was professional and didn’t make a stink about things. Despite the all consuming desire to stick with what I know, the decision was really a no-brainer. It was time to go.

I walked in to Maggie’s office on a Tuesday morning and told her that I had accepted a position outside the field of childcare. She did not seem surprised in the least. I had kept it from her as long as I could, but when I had to do the Zoom interview, I ended up having to come clean because I needed to be sure someone could cover me on the floor if the interview ran long. She congratulated me and I went to the bathroom and cried.

I gave her two and a half week’s notice. I wanted as much time as I could have to train the new staff who would be replacing me in the program, as well as more time to cherish with those babies. I’m literally writing this through tears. I truly can’t express it enough how much I really did love them and how much I loved working in that program. This was one of the hardest decisions I had ever made, but at that point, there was no turning back.

What made it easier, however, was seeing the owners scramble to save their asses as they offered me all sorts of things in order to stay. They offered me the Director position at a different location in the west end of the city. As tempting as that was, where was that offer when I had applied for the promotion in the first place?? If I’m so great and wonderful and talented, and that other location is in such dire need of an overhaul, why was that position not offered to me from the start? They asked if there was anything they could do to keep me, and even offered me Maggie’s position when she threatened to quit too. (That’s another thing – they treated Maggie like shit. Expecting so much from her with little to no training in the position and literally no help in her attempts to fix all the problems the centre was having).

Thanks but no thanks, ladies. Sucks to suck. If I had been offered these things right away, I would have gladly accepted and would have likely worked in child care for the rest of my life. Too little, too late, though. This was just another sign from the Universe that it was time for me to move on.

Those two weeks flew by in a flash. All of a sudden it was my last day and all my amazing co-workers were making me cry in the cubby room. They arranged this beautiful basket for me full of positive affirmations for days I may second guess myself, an I.O.U for a girls night since we hadn’t been able to arrange one before I left, and even some pre-rolls from the nearby pot shop. These bishes know me too well! If any of you are reading this, know that I miss you all, and I love you. And I can’t wait for our girls night out!

My last day was a Friday. I left early as I had had plans to attend my cousin’s bachelorette party out in wine country. I knew I had an emotional five hour drive ahead of me, so I gathered all my belongings, hugged my co-workers/amazing friends, loaded up my car, and headed out. I put on my Pandemic Tunes playlist on Spotify and psychic shuffle really came through. Songs came on that made me cry, made me yell, made me groove, and made me think. I’ve always loved a road trip, but it was again, a way for the Universe to show me that I did, in fact, make the right decision. And one thing I’ve learned in recent years is that more often than not, the right decisions are usually the hardest to make.

I’ve started my new job now. It’s like I’m on an entirely new planet. Different doesn’t even begin to describe this job compared to childcare. But the people are so generous, helpful and kind. The job itself will become easier as I get used to it, and again, the money and benefits are second to none. I’ve worked so hard on myself and I’ve come so far. Now this new job is the gateway to the life I’ve always wanted. And who knows? Maybe a home daycare is in my future. You know, the home that I’ll buy with all the money I’m making at this new job 😉

Anyways, I guess the point of all this is A) I needed to process all these changes and this is my outlet to do that, but B ) it’s also a reminder to anyone else in a similar situation, whether it be personal, professional, whatever. All the best things in life are just on the other side of fear. You can’t let the fear of the unknown deter you from pursuing the life you want and know that you deserve. No one else on this planet can make things happen for you. It’s all on you, girl. So take the leap and go for it. You’ll be surprised when you land on your feet and have a whole new life ahead of you.

For more adventures and mis-adventures in dating, Stay tuned Wednesdays at 8pm EST

Chapter Fifty Seven

The same Saturday that she had reached out to Wyatt with a little waving emoji, she of course had kept chatting with other guys online (Clearly she needs a hobby). But in continuing with her dating apps, she matched with one of the hottest guys she had seen. He was tall. He was broad. He was 45 and had a great smile. We’ll call him Greg.

Greg was enthusiastic and eager from the second they started chatting. He had this youthful excitement about him. Everything she said seemed like a breath of fresh air to him. But it wasn’t long after starting their conversation that he turned things towards sex. She was fine with that. It wouldn’t be the first time she dirty talked with a guy online. But it was the way he phrased the questions, how he asked them… For a guy as hot as he was, he seemed to have no game whatsoever.

He wasn’t smooth. He was clunky, if that makes sense? She got the distinct impression that she had way more sexual experience than he did – a feeling she wasn’t used to having. As they touched on to more and more sexual topics, she uncovered that his personal life was far more complicated than she could have expected.

Turns out he was married. Well, separated, not divorced. And still living in the same house as his (ex)wife, after having ended things two years prior. He explained that they were continuing to live as a family unit in order to keep some semblance of normalcy for their two children. A noble thought, but kids aren’t stupid. What an awkward living situation for that entire family. He also expressed that he knew his (ex)wife was seeing someone because she had been going to “yoga” for six hours a session every couple days for over a year. He, however, had still yet to meet anyone of any significance.

Holy. That was a lot of pressure on her, all of a sudden. To be the first person someone dates while dealing with something like that, it felt heavy for her. Still, he was so sweet, and she kind of felt bad for him. Also, let’s not forget how hot he was. He was super friggin hot, keep that in mind. So she continued chatting with him while trying to keep his expectations low. He had openly expressed several times how excited he was to have matched with her, and asked more than once, “so you’re willing to give this a shot?”

Give what a shot? Dating? Starting a real relationship while you still live with your wife? The only thing she was willing to do was meet for a drink and see how the night went. She felt like he was way more in to this than she was, but again, she felt like he had just been out of the game for a while. She found his innocence somewhat refreshing and charming, if also a little clumsy.

They had realized that they actually both lived in the same end of the city, which was rare. Usually people were at least a half hour’s drive from her. This guy happened to live right up the street. Because they lived so close, he got himself caught up in this fantasy of meeting up for a quickie in his car. She had told him that there was no way she was hooking up in a car the first time they met, if ever. She had done the car-hookup-thing in her early 20s and she knew from experience that there was no way she was getting off in someone’s backseat. She was at a place in her life where her sexual pleasure was her priority. Gone were the days of faking it for guys just to stoke their egos. Thus, no car sex.

This presented a problem for their hypothetical future sex life. She lived with her parents, he lived with his wife and kids. If there were anything sexual to happen between the two of them, it would have to take place when no one was home at his house (which was rare, he said), or at a motel room as he so chivalrously suggested. He seemed exhilarated at the thought of being like teenagers again. She, however, was less than thrilled.

He continued with all sorts of fantasies that he’d clearly been obsessing over throughout the past two years. She was flattered that he was so in to her and so excited to try all these hypothetical sexual activities with her. But again, she tried to keep his feet on the ground and his head out of the clouds. She told him not to get his hopes up and that there would very likely be something that would happen to prevent things from really going anywhere between the two of them. Her dating experiences had apparently left her glass-half-empty. He replied that he was a natural optimist and that he had a good feeling about her. That was refreshing to hear, actually. And it made her feel less nervous about meeting him, which seemed odd considering she felt his expectations were so high.

She finally got him to cool it on the hypotheticals and to commit to actually meeting up. They agreed to meet for drinks at 8pm that Friday at a bar close to both of their neighbourhoods. She was skeptical about how optimistic he was about everything, but she was still willing to see what he was like in real life.

The rest of her weekend was uneventful and boring. She worked out, got stoned a bunch of times, watched Netflix. Really livin’ the life. You can imagine how excited she was, then, when she randomly got a text from Kyle on that Sunday. “Hey you!” It read. “I know it’s late, but I was wondering if you were free to hang out this afternoon?” She one hundred percent did a happy dance in her kitchen.

It had been just over a month since she had spoken to Kyle. The last time they had seen each other, the sex wasn’t as mind blowing as it usually was, and he napped almost the entire time she was over. Yes, she was fine with it, but it was definitely not what she had hoped for when she had gone over that day.

And now, here he was, texting her after so long and asking her to drop everything she was doing (which was fuck all) to go over to his place to have sex. Did she want to? Abso-fuckin-lutely. But there was no way she could maintain any level of integrity if she jumped at it as soon as he poked his head back in to her life. She waited a while before replying with, “Oh wow, hey. Sorry, I can’t tonight. Another time, with a little more notice ;)” She felt like she had handled that pretty well. It was made it clear she was still interested, but that she wasn’t at his sexual beck and call. He replied with “Sounds good” and a kissy wink face.

Fuck. Yes! she thought to herself. Kyle was back in the picture.

That Friday as she was heading out to meet Greg, he texted her asking if they could meet at 8:45 instead. His (ex)wife had let their son have a friend over, and he was volun-told to drive the friend home at 8:30. She was annoyed, but she always tried to be understanding when it came to kid stuff. She told him “no worries” and decided to do some errands before meeting him, which she had originally intended to do the next morning. Still, she was at the restaurant about 20 minutes earlier than he was. She went in and got a table, people watching and sipping her water as she waited for him.

Finally, she saw him walk in. He was so tall, she could see the top of his head over the partition between the entrance and a booth. He wore a nice salmon coloured button down, tucked in to a nice pair of jeans, complete with some very classy brown loafers. You knew he was a dad, but he was a hot dad. He turned and saw her leaning out of her booth like a damn fool. She laughed and waved as he headed over to her.

He sat across from her and smiled, not saying anything. “Hiii!” she said as she gave a dumb little wave. He blushed and looked down, softly replying, “Hi” back. What the hell?! she thought. He’s so shy!! She wasn’t used to guys being so… submissive, for lack of a better term. But really, it’s true. She was used to guys being strong, masculine, take-charge types. Not shy, introverted, blushing types. She tried to start a conversation but for everything she said, he’d just laugh sweetly and smile blankly back at her. Eventually she literally resorted to whipping out a 20 Questions list on her phone just so they’d have something to talk about.

The game worked. He opened up about himself like where he was from originally, how he had a twin, and oh, how he was in a horrific car wreck when he was 9 and spent like 7 months in the hospital – y’know, casual first date conversation. It seemed like any time he did speak, he said something more surprising than the last. Soon she found herself opening up about funny sexual experiences she’d had just so she could control the conversation again.

This was the stuff he was interested in. He listened intently as she regaled him of her sexual escapades since becoming single. Even some stories from her past like her mortifying high school grad trip to Mexico (which we skipped over in the blog. It’s not in here, and it never will be), or the time she and her ex “swung” and swapped partners with another couple. She elaborated on how the guy from this couple was so hot but unfortunately had a small… unit. She gestured with her thumb to humourously indicate his small stature.

They chatted over several beers and, you guessed it, a shared plate of nachos, before Greg actually got up the nerve to ask, “Hey so… think you might wanna go make out somewhere?” Where? she thought to herself, realizing it would likely be in his car. She weighed her options and decided she was fine to just go make out, but knew she wasn’t going to have sex. But like, she REALLY knew it this time. She definitely wasn’t going to have sex with this guy in his car.

He paid their bill and escorted her out of the restaurant and towards his BMW convertible. She was surprised to see he drove a Beamer. Her experiences with guys who drove Beamers had been less than pleasant, to say the least (ie: Beamer Boy, Chapter Two). She couldn’t deny it though, it was a nice fucking car. She got in and they started driving out towards the country in search of a dark side road on which to pull over so they could fool around. Did she think about the possibility of her getting raped, murdered and chopped up in to little pieces? Why yes she did, in fact. Clearly, though, she felt the risk was low, so she took her chances.

While driving out there he confessed that it had been about 3 years since he had had any physical contact with anyone. For the last year of his marriage, he and his wife didn’t have sex, and then for the following two years living together, he still hadn’t gotten himself any action. She knew he hadn’t dated, but no sex whatsoever?! She was surprised, but that explained a lot about how awkward he was.

After driving for about ten minutes, they found the perfect spot to pull over. They both pulled their seats forward before crawling in to the back. Immediately his hands were all over her as if he were a frantic airport security person patting her down for contraband. He tried to grab her boobs but couldn’t fit his hand between her and her bra. She graciously whipped it off, keeping her shirt on, to give him better access. She was so used to the guy being in control during her sexual encounters, it felt awkward when he didn’t take charge. So she did.

She started kissing him and getting things going. He was even an awkward kisser. He felt her up for a while, as her hands remained away from any of his parts. He moved his hand down to her legs, so she moved hers down to his. He then tried to rub her over her pants, basically grabbing a fist full of her “fupa” in the process. She stopped him and just flat out said, “It’s not gunna happen. Not for me. But just relax, I’ll help you out…”

She wasn’t sure what came over her, but she just knew that this guy needed a night of fun. At least one moment’s pleasure to break through the shit storm that was his life. She started to rub him over his jeans and found he was already quite alert. He unzipped his pants and pulled them down just enough for her to get a grip. She was very taken aback by how little she had to work with. In that moment it made sense to her why he drove this kind of car. Clearly he was compensating. How could this giant man have such a small package?! On top of everything else he had to deal with?! This poor man!!

She kept going for a few minutes, finding it more and more difficult to get anything going. “It’s not gunna happen…” he finally said. “What do you mean?” she asked. Surely he would be able to get off after not having done this in so long. Well, in fact he did.

“Well,” he clarified, “it’s not gunna happen again, I mean…” Turns out that within seconds of her starting, he came. She had felt something on her hand, but it was dark and there was so little of it she didn’t think he possibly could have finished already. It was then that he grabbed the only thing he could think of, his disposable mask, to wipe up her hand and himself.

In her head, she was dying laughing. It was the mask wipe up that pushed it over the edge for her. But she kept her composure, especially when he began to apologize profusely for finishing so quickly. Truly, though, she was unbothered. It was actually nice not to have to do that for as long as she usually would have to. And even after all that, she felt like there still could be something there. He was so kind and honest and sweet and he clearly thought she was the bee’s knees. Maybe she could still work something out with this guy.

He drove her back to the restaurant where her car was parked, and told her he’d text her later. They kissed goodbye and she got out of the car. She drove home, washed her hands immediately, then went out to the garage to smoke a joint before bed. As she puffed away, he texted her. “Hey! Hope you made it home ok. I had an awesome time tonight. Thank you :)” She replied saying she had a nice time too and joked that she was happy to help. It was then, though, that he ruined everything.

“Am I bigger than a thumb?” he asked her.

Oh. Em. Effing. Gee. In that moment she wanted to just crawl in to a hole and die. She had forgotten she had said that, and of course when she said it she had had no idea how small he was! Not wanting to shame him any further than she unintentionally already had, she replied “Yep!” but didn’t elaborate. Then he texted, “Do you think you’re going to like it?”

She wanted to throw up in her mouth. Never had she been so turned off in her whole life. All of a sudden she realized what it must have been like to be on the other side of her own insecurities as a teenager. It was so unattractive! She didn’t want a guy to ask her if she was going to like his dick, she wanted him to tell her she was going to love it! And yes, most guys that do that are equally as unattractive. But when it’s the right guy, a guy she had chemistry and a connection with (a guy like Kyle, for example), being told what to do or what she would like, was one of the hottest things a guy could do.

Up until that point she hadn’t fully written Greg off. Even though he was as small as he was, she was trying to be optimistic in thinking that there were other ways he could please her that didn’t involve his… little soldier (trying to think of clever euphemisms for the word penis is harder than you’d think) [ha, “harder”… penis… never mind..]

But yea, after that, she was completely turned off. She waited 10 minutes trying to think of something kind yet clear that she was over this. She was stoned and couldn’t get her thoughts straight so she just sent out another “yep”. He liked her comment and she tossed her phone away from her. Fuck. At that point she was pretty sure Greg was so in to her that he was already planning their wedding. Now she had to figure out how she was going to get out of this…

Continue to Chapter Fifty Eight

Chapter Fifty Six

The following Saturday after her date (and subsequent reluctant hook up) with Mario, she had matched with yet another guy on Bumble.

His name was Wyatt, and he was several years older than her. It was a nice change from all the younger guys she had been matching with. He had great scruff, a great smile, a thin build, and was decently hot… even though he was only 5”9. She sent him a little wave emoji to start their conversation, and once he replied, she got good vibes from him right off the bat.

She had had plans that had fallen through, so she casually mentioned to him that she had been hoping to go out for a drink that night. He took the bait and replied that he lived right in the downtown core and that he would love to meet for a drink if she were interested. She was relieved that her night had taken a more exciting turn than just Netflix and Chill-ing all by her lonesome, and replied that she would be happy to meet up with him.

They arranged to meet at 8pm, but she arrived closer to 8:30. She had gotten stuck in construction traffic, and then struggled to find parking on the chaotic downtown streets. She texted him that she would be late and he was very understanding. As she approached him, her immediate thought was that he looked very similar to her ex. They had the same build, and were both on the shorter side. She thought she would regret the date as soon as she got there, but he could not have been more friendly or charming.

They headed over to check out a restaurant but found that the wait was too long. They put their names on the wait list but decided to grab a beer at another place a little further down the block. She hadn’t been to this other pub since her early 20’s. Blurry memories of many a drunken night flashed through her mind.

They sat at a high top and started to get to know each other. She found out that he was a graphic designer for an advertising agency, and that they shared a lot of similar interests in regard to art and culture. This was one of the more stimulating first date conversations she’d had. She loved when she was able to talk art with someone.

They finished their beers and decided to take a little walk just outside of the downtown core to go smoke a joint. She also wanted to show him a cool art piece she knew of, which she was surprised he hadn’t seen yet considering he lived so close. The art installation were these giant plywood cubes, each decorated with different murals all over them. Each side was something else, a different style than the last. They puffed away and appreciated the different techniques.

Afterwards, they went back to check on their table at the first restaurant. Once they got there though, they decided it wasn’t the right vibe, so they strolled along through the bustling downtown streets in search of somewhere else to settle. They chose a popular Irish pub on one of the main streets in the area. The patio had been extended in compliance with Covid protocols, so they had a lovely view of a lamp post and a fire hydrant directly next to their table.

They ordered beer and nachos, which she realized was becoming her staple first date order, and continued on with their enchanting conversation. Just like most of her other first dates, the conversation flowed and she was enjoying Wyatt’s company. She found out that he had recently gotten out of a relationship only a few months prior. Also that his dad had passed away when he was a teenager and that it was just him and his mum now. He was an only child, but had friends who are like family, whose children call him Uncle Wyatt. They talked for hours. Both of them acknowledging that they were having a great time and that neither of them wanted the date to end.

After finishing the nachos and their second beers, they decided to move the party to a dessert restaurant a few streets over. They each ordered a deliciously mouth-watering slice of Oreo cheesecake (made in house), as well as some decaf cappuccinos. They sat on the patio, which was also extended out in to the street, and just people-watched. Commenting on the crazies, commenting on people’s outfits, and just acknowledging how strange it was to be living through this specific period in time. They finished their cake and again, neither of them wanted the date to end, so they took a stroll through a nearby park.

After they had literally gone everywhere they could have in hopes of extending their time together, she decided it was time to pull the plug. It was nearly midnight, after all, and she knew for one hundred percent certainty that she was not going back to his place. She was done making that mistake.

He walked her to her car in the big parking garage near the restaurant. As she turned to face him, she saw how nervous he was and she knew he wanted to come in for a goodnight kiss. She made it easy for him and stepped forward. He leaned in for the cutest, most awkward first kiss ever.

He tilted his head the same way she did, their noses bumped, and he wasn’t sure what to do with his hands. “Ah!” he said as their lips parted. “I’m sorry! That was my first first kiss in a long time. I’ll do better next time!” She giggled and told him it was fine. She had a really nice time and she was looking forward to seeing him again. He told her he would text her, but based on her track record for second dates, she wasn’t about to hold her breath.

You can imagine her surprise and delight, then, when she heard from him the very next day. They had talked about their mutual love for Marvel movies, so in his text he invited her to see a movie the following weekend. She agreed, and was shocked and excited at the prospect of actually having a second date with this funny, charming, attractive, 41-year-old man. Could this actually be the beginning of something real?

They texted here and there throughout the week, and when Saturday arrived, they confirmed that they’d meet for dinner and drinks around 8pm, and then see the movie which was playing at 10:10pm.

She was at a family function during the day, and had been regaling her cousin with the tale of this apparent unicorn of a man whom she was supposed to meet up with for a second date. Around 6:30pm he texted her in hysterics. He said that all his passwords had gotten hacked; his e-mails, his social media, even his Netflix account. He sent her a pic of his now Spanish Netflix home page. He frantically asked if she would mind postponing their date until the next day. Unfortunately, she had another family function the next day and wouldn’t be able to reschedule.

She felt the air burst from her figurative bubble. She should have known better than to get her hopes up for an actual second date. Granted, he did seem to have a genuine problem and it didn’t seem like he was just flaking on her. She told him to message her if he was able to sort things out sooner rather than later. She spent the rest of the evening bitching to her cousin about dating in general, over several glasses of wine.

She messaged Wyatt the next day to see how things were going. He didn’t reply until Monday morning while she was at work. He said that he had sorted out his e-mail issue, but was still working on his Netflix and social media. “I’m so, so sorry about Saturday!” he said. “All good, shit happens…” she replied. “I’m still down to get together sometime, though, if you want?” He had his Read Receipts on so she saw that he had seen her message, but he sent no response.

NOW she was pissed. How is it that even when she didn’t have sex with someone, she still gets fucked over?? This guy seemed like he was so in to her! More than she was in to him, that’s for sure. He was awkward and cute and goofy around her, and he seemed genuinely apologetic about canceling, as well as wanting to reschedule their date. What happened in those two days that could make him change his tune like that??

The week went by and she distracted herself with other dating app guys, but on the weekend when she was home alone, bored and stoned, she was going through her phone and just messaging random guys she had in her contacts. She came across his name and decided to send just a little wave emoji to see if he’d respond. Again, she saw that he had seen her message, but no reply.

Later that next week, as she scrolled through Instagram when she really should have been working, low and behold, what did she see? A 2-pic-post by Wyatt of him and, presumably, his ex-girlfriend.

The caption read, “Best Monday ever! #minigolf #monday #love #sunshine”, with a comment from the girl saying, “I had so much fun! Thanks for the most amazing day, amor”. As well as a comment from someone else saying, “Such a beautiful lady,” and Wyatt replying, “She’s amazing!”

What the actual fucking fuck!?!?

A week ago he was smoochin’ her in a parking garage, now he’s back with his ex?! Of course, it could have not been his ex, but who falls in love with a new person in a week? Was this the real reason for the canceled second date all along? Or did he actually have those password problems, and then just happened to reconnect with his ex later that week? All she knew for sure was that regardless of whether or not she had sex on the first date, guys in general are just shitty fucking ass holes.

That’s all. That’s the end of this chapter. Fuck that guy and his #love.

Continue to Chapter Fifty Seven

Chapter Fifty Five

A few days after returning home from her vacation, she matched with a super hot Italian guy on Tinder. Not Italian from Italy. He was definitely Canadian, but with all those sexy, dark, Italian features. They chatted about work, their interests, what they were each looking for in regards to online dating. She made it clear that she was not looking for just a hookup. She was sick of meeting up with guys, having sex, and then never hearing from them again.

She told this hot Italian guy – let’s call him… Mario (haha) – that she was looking for a Friend with Benefits, but big emphasis on the Friend part. She explained that she wanted someone she could have fun with. With whom she could go on dates, go out for dinner, go to a movie, see a comedy show, whatever! But without getting too serious.

Serious, to her, meant meeting friends and family. She was no where near ready to fall down that rabbit hole of questions and advice and all the other bullshit that comes from integrating a new boyfriend into one’s life. Mario seemed to be totally on board with that. He, too, said he wanted to meet someone to have fun with, but wasn’t necessarily looking for something super serious either. (A guy on a dating app only looking for fun?? Shocking!) It seemed like they were on the same page, so they arranged to meet up that coming weekend.

Their tentative plans were set for Friday, but she had to cancel as she had forgotten she already had a prior commitment. They rescheduled for Saturday.

Saturday morning came and Mario texted her saying his family engagement was going to run longer than he had expected, and was hoping she was free the Sunday instead. Rescheduling dates this much is usually a red flag, but she still agreed to meet on the Sunday instead.

Sunday morning, she texted him to confirm their plans and he assured her that he was down to meet up that day. He asked where she wanted to go grab a drink, but reiterated that he was happy to host her at his place with some weed and wine. As enticing as that was, she knew if she just went to his place that they would end up having sex. She was determined to wait, at least until the second date, before getting intimate with another guy.

“Let’s see how drinks go first…” she replied. He laughed and suggested a great bar downtown, which just so happened to be a stone’s throw away from his apartment. She agreed to meet outside of his place so she would have somewhere easy to park, and they’d walk to the bar from there.

She jumped in the shower and as she washed her body, she made the conscious decision not to shave anything. (Built in birth control, right ladies?? ) This would ensure that no matter what, she would not be taking her clothes off with this fella. She finished getting ready and told her parents she was meeting a friend downtown for lunch.

She punched in his address and headed out. When she arrived, she was confused because the building she had stopped at was the apartment building in which one of her friends used to live. She texted him to ensure she was in the right place, which she was, and he replied that he would be right down.

When he came out the front doors, her stomach tied in it’s signature knots. The feeling she got whenever she was overwhelmed by someone’s attractiveness, combined with immense nervousness about making a good impression. He greeted her, complimented her, and they headed over to the bar. They were immediately seated on the patio and they both ordered a beer. The conversation flowed like water. No awkward silences, no forced chit chat. They were both genuinely interested in what the other had to say.

They laughed, they exchanged stories, and he surprised her not only by not teasing her when she mentioned that she was an emotional Cancer – he even knew what his own zodiac sign was (Gemini), as well as his Moon and his Rising (which were both Cancer. Bonus!!) She couldn’t believe how well this date was going. They decided to order nachos to share, as well as another beer each.

They had to have been there for over two hours. It was one of the most enjoyable afternoon’s she had ever spent with a stranger. They finished their second beers and he asked if she wanted to go over to his place to smoke a joint. She hesitated, but he really did seem like he was on the same page as she was. She figured one joint wouldn’t be so bad, especially if it meant this date didn’t have to end. She was genuinely enjoying his company.

They walked the five minutes back to his place, and as they got in the elevator and he hit 12, she was overwhelmed with an uncanny sense of déja vu. It was several years ago, but she was certain that her friend had also lived on the top floor.

They got off the elevator and turned left. The déja vu feeling became even more intense. “That’s not your place, is it?” she asked as she pointed to the upcoming door to her right. The exact unit she remembered to be her friend’s old apartment. “Yeah it is, how did you know??” he asked.

He unlocked the door and she basically walked back in time. It was completely mind boggling to her that this guy lived in her friend’s old apartment! She told Mario about the coincidence, by which he was also blown away, but she texted her friend just to be sure. Turns out her friend had lived in that exact unit, but one floor down. So it wasn’t exactly the same apartment, but still close enough to warrant her bewilderment. Just another example how small town that big city was.

He gave her a little tour of his place, which she really didn’t need since it was a replica of her friend’s old place, before bringing her out to the balcony. He had an absolutely breathtaking view of the city. As she gazed out over the many buildings, he turned her attention to the right to show her his incredibly gorgeous pot plant. It was big and bushy, and almost ready for harvesting. This guy just kept getting better and better!

They came back inside and he offered her a glass of wine. Since she had already had two beers at the bar and she still had to drive home later, she asked for a glass of water instead. He went in to the kitchen and she followed slowly behind him, looking at all the war memorabilia he had displayed on his walls. He handed her the water and darted quickly into the living room.

Before she even had a chance to take a sip, he was back in the kitchen, inching closer to her, giving her major make-out vibes. She looked up at him and unconsciously bit her lip. This was the only invitation he needed to fully come in for a kiss.

It was a great kiss. Strong and forceful, yet soft and tender. He started running his hands down her back, onto her ass. Shit., she thought. But that wasn’t enough for her to make him stop. She was in to it, so apparently over the clothes was allowed.

The kissing became more intense and he started running his hands over other parts of her body. She could feel the butterflies building. She could feel her knees weaken. She knew what he wanted. And she knew she wanted it too. But no! She had promised herself she wouldn’t.

She tore her lips from his and asked him in a sexy whisper if he wanted to smoke that joint. He smirked and looked down at her. “Are you sure you really want to smoke now?” he asked as he kissed her again. Before she knew it, he was pulling her towards the bedroom.

Yes, she could have stopped it. Yes, she could have said no. But aside from this stupid friggin promise she had made to herself, there was also a part of her that really, really wanted to! She enjoyed sex. She had resented sex for so long when she was with her ex, so when the opportunity presented itself, it was hard for her to resist.

He guided her backwards onto the bed, and they continued to make out for several minutes. But sure enough, the clothes started coming off. Alarms went off in her head about her hairy legs and bushy bush. “I forgot to shave!” she blurted out. He paused and looked down at her from where he was kneeling between her legs. He smirked and said, “It’s all good. I like a little hair…” That was all she needed to hear to allow herself to fully surrender. After some fairly decent foreplay, they started having sex.

It was good. It wasn’t first-time-with-Kyle-good, but it was good. He kept telling her how hot she was, how amazing she felt, how much he liked whatever it was she was doing. She felt sexy and confident and was able to really enjoy herself.

Once they finished, he lay on his back, his arm stretched out for her to come nuzzle in to his nook. They lay there together just basking in that post coital haze. They talked about getting together again, and how they felt that they were each happy to be on the same page as one another.

After a few minutes, though, Mario got up to go to the washroom. As he walked out of the bedroom he said, “Oh wow. I didn’t realize the time. I’m meeting a friend to watch the UFC fight soon…”

She bolted upright and immediately got herself dressed. A flood of rage consumed every molecule in her being. “How soon?” she hollered to him. He came out of the bathroom and casually replied, “Oh, about half an hour – 40 minutes?” Basically telling her that it was time for her to leave.

She couldn’t fucking believe it. And yet, she wasn’t surprised. This was exactly what she had been trying to avoid by making a pact with herself not to have sex. She maintained her composure and told him that she had to fix herself up again before she left. Fortunately, she had put her travel sized hair straightener in her purse a few days prior, so she was able to fix her sex hair before going home to her parents.

As she got ready in the bathroom, he stood behind her in the doorway and they went right back to the comfortable, casual conversation they had had at the bar. She was annoyed at how much she still liked him, despite this predictable “wham-bam-thank-you-ma’am” situation. She took her sweet ass time fixing herself up. When she was ready and had gathered her things, he kissed her deeply at the front door and told her he’d text her that week to arrange another date. She smiled at him as she left, swallowing her rage as he closed the door behind her.

She got in the elevator, and in her mind, she was went completely ape shit. You know in movies when you see a character completely lose their shit? Throwing chairs, smashing mirrors, breaking anything and everything in sight? And then the scene changes and you realize that was all just in the characters head? That’s exactly what was going on with her. The elevator doors dinged open and she snapped back to reality, nodding politely at the older lady who was boarding the elevator as she got off.

She got in her car and began to drive home. She was almost in a state of shock. Within only a few minutes, the amazing, casual, fun afternoon she had just had with this seemingly awesome guy, had been shattered. She was once again faced with the reality that once a guy gets the sex he wants, good luck ever hearing from him again.

She tried to hold out hope that this guy was different. He had said he would text her to arrange another date. Maybe he would actually follow through?

Monday came. Then Tuesday. And by Wednesday when she still hadn’t heard from him, she made the leap of texting him herself. She told him the days she was free that week and wondered if he still wanted to get together. He replied that his week was pretty hectic but he’d be down to hang out the following week instead.

Of course, she thought. She knew that would be it for him. She wasn’t about to hold out hope that he would message her, but found it ironic that he would still creep her InstaStories as the days went by.

Two weeks passed since that conversation and, sure enough, he never texted her. One Thursday afternoon, she had been planning her weekend and knew that she would be downtown with some friends the next evening. She thought it might be nice to meet up with someone afterwards for a little x-rated fun. She messaged a couple guys she had on her roster, one of whom was Mario.

He replied fairly quickly and seemed interested in meeting up. He was also going out with friends that night so they agreed to text each other when either of them knew their final plan for the evening. She knew her night would be done sooner than his would be. She messaged him around 10pm letting him know. Unsurprisingly, he was still out and wouldn’t be available to meet up any time soon. And that was it. She was officially done with this guy.

A couple days after her original hook up with Mario, she had matched with a hot 41 year old guy named Wyatt. Maybe he would be the one to turn her dating life around?

… or maybe not.

Continue to Chapter Fifty Six