After her disappointing second “date” with Jon, and ol’ Needle Dick having unfollowed her on Instagram, she felt completely uninterested in dating whatsoever.
It was now January 2022. Another lockdown. Another month of work, then home, and back again. What would have been the point in dating? She had turned off all her notifications from all her dating apps, but sometimes would find herself going a little stir crazy, so every now and then, she’d check in on the sad selection of guys her apps had at the ready.
She opened Hinge, and found a guy named Jack had sent her a “rose”. She checked out his profile and, according to his answers to the prompts he chose, he really did seem like an interesting fella. He came off as charming and confident and funny and sweet. However, he looked like the Canadian version of Pauly D (Jersey Shore). Hair not quite so hard and helmet like, and skin much less orange, but that same greased up sleaze ball look. The gold chain was the cherry on top. She really debated whether or not to match with him. Physically, he didn’t seem like her type, but his answers were great and she knew that her “type” never ended up being good for her. So she took a chance and matched with Jack.
It was a day or two before he sent her a message. Again, he was charismatic and funny and charming. Turns out, he lived somewhat on the outskirts of the downtown core, but was house/dog sitting for his friend who lived close to where she worked in the west end of town. He asked if she wanted to come by one night. She appreciated the interest he had in her, but didn’t feel comfortable meeting for the first time at a strangers’ friend’s house. Instead, she suggested they meet for coffee at the Starbucks near her work. If they hit it off, they could see where things went from there. He agreed, and they made plans for that coming Friday.
She arrived at the Starbucks before he did, but knew that the big, black pick-up truck that pulled in a few spots down from her, had to be him. He got out of his vehicle and started walking towards the building. He met her gaze as she spotted him walking, and she got out of her car to greet him. He wanted to go in for a hug but she goofily dodged it in to an elbow tap. Even though she had hooked up with several guys throughout the pandemic, she still tried to be cautious upon first interactions. They went and ordered their coffees, and he gallantly offered to pay. That might not seem like a big deal, but she really never did expect her dates to pay, and Starbucks is expensive! So it was a pleasant and welcome gesture on his part.
She wasn’t sure what the plan would be from there. Because of lockdown, they couldn’t sit and chat inside, but it was January so it was still cold AF outside. A stroll around the block was also out of the question. He suggested that they keep warm in his truck. On one hand she thought, “What if he drives away and kidnaps me?!”, on the other, more logical, hand, she knew the odds of that actually happening for real, were pretty low. She agreed and climbed in to his truck to drink their coffees and chat.
She noticed right away that he was nervous. He wouldn’t shut up. Even when he’d ask her questions, she’d start answering and then he’d interrupt with his own anecdote. Yes, that was frustrating and very mansplain-y of him, but she could tell it wasn’t coming from a rude place. He seemed genuinely interested in her. And still, she couldn’t decide if she was in to him or not.
As a friend, she knew he’d be great. But as anything more, she was still on the fence. That alone should have been her red flag that no, she wasn’t in to him. But again, every guy she *was* in to, turned out to be a total D-bag. It was the fact that she wasn’t super in to him that made her want to try harder to find something romantically interesting about him.
They chatted for a while about this, that and the other thing. Obviously they touched on sex. Jack boasted politely about his sexual prowess. He told her that of the few girls he had been with, they had all told him that he was incredible in bed. She knew that for him to say that meant that he likely wasn’t the sex king he claimed to be, but she let him continue with his narrative. It was then that he mentioned that he hadn’t lost his virginity until he was 35 years old. THIRTY FIVE! (She thought her losing it at 22 was late) If she wasn’t sure before, she definitely was now, that he most certainly was not the sex god he said he was.
They talked until it got dark. Despite his lack of experience in the bedroom, he remained a fairly interesting conversationalist. Still, if he had invited her back to his friend’s place, she probably wouldn’t have accepted. Thankfully, she didn’t have to make up any excuse because, and these were his exact words, “I’d love to have you over, but truthfully, I bailed in the shower earlier and I tweaked my neck. It hurts to just turn and look at you, so I really should go home and take care of this…”
She tried so hard not to laugh. Not that she found his pain funny, but that is just such a believable excuse. Definitely something she would do and could relate to. He got out of the truck and she allowed him a quick little goodbye hug. He was tall and brood, so for the split second that he had her in his embrace, she thought, “hmm.. maybe there could be something here?”
They said their goodbyes and she then broke every speed law imaginable trying to get home before she peed her pants. He had ordered her a Venti and she drank the entire thing, but couldn’t pee at Starbucks because of lockdown. She had never rushed home from a date faster than she did that night. (Don’t worry, people. She made it in time 😉)
During their truck chat, he had asked about getting together again sometime. She suggested the next day seeing as it was lockdown and she consistently had zero plans, and even though it likely wouldn’t be the sexcapade of her dreams, she seemed to be enjoying his company. He, however, did have plans, so they just left it open ended.
Saturday, early afternoon, he sent her a message and they got to chatting again. He had said that his plans got canceled and asked if she still wanted to get together. It had been a very lazy Saturday so she was still in her PJ’s, but it was only like 5pm. She had plenty of time to shower and get ready, so she decided to take him up on his invite. She told her parents she was off to see a friend, punched the address into Google Maps, and headed on her way.
When she arrived at Jack’s friend’s place, her jaw dropped. It was a literal mansion. Like, 10 car driveway, double front doors, grand entrance, spiral staircase, 10 bedrooms, 7 bathrooms… truly, a fucking palace. He gave her a tour of the main floor, and as they strolled in to the living room, she saw a beautiful, old, grey Pitbull curled up on the couch, wearing a cone of shame.
The dog had just had emergency surgery before his friend had to go away on business and needed extra care while he was away, so Jack was there taking care of her. Okay, major hot points right there. They sat on the couch and put on some random stand-up comedy special on Netflix while they got to talking. The dog took to her immediately and crawled right over to her, positioning herself between her and Jack. She was kind of relieved by to be honest, because then Jack couldn’t put any lame moves on her.
Eventually, Jack suggested he give her a tour of the rest of the house. She accepted, knowing full well they would end up in the bedroom. She knew that if she had said no to having sex that Jack would have respected that. She could just tell he was a genuinely nice guy, which is probably why she wasn’t super in to him. That, and the fact that she couldn’t get his lack of sexual experience out of her mind.
When they got to the bedroom, he inevitably tried to kiss her and get things going. She decided to just go with it. Who knew? Maybe he had learned something from the few girls he’d hooked up with? Maybe he would blow her away with his “incredible” bedroom skills (his word, not hers) and then finally she could prove to herself that she was capable of finding a genuinely good guy to be with.
The kissing was decent. Which then led to foreplay, which was not so decent. Very rushed. Not nearly enough time was spent getting her warmed up. Then, before she knew it, condom was on and they were having sex. Missionary style seemed to be his preference. And while that’s all well and good, having this strangers’ face right up against hers while he panted and grunted and thrusted away, just really wasn’t doing it for her.
She suggested they switch things up and start with some doggy style. At least that way he wouldn’t be all up in her face. Unfortunately for Jack, “Little Jack”, had quite the significant curve in it. Like, it literally looked like a small banana the way it curved up so much. “Maybe that’s why he was a virgin for so long?” she thought. “Maybe he had crippling insecurity over his banana dick?” (Get your head back in the game!)
Jack had been able to maintain a good rhythm while doing it missionary. However, after switching positions, Jack didn’t stand a chance. He finished in record time, and she realized then why he preferred missionary; his curved weiner was just way too sensitive any other way. He hurried off in to the ensuite bathroom to clean himself up, while she got herself dressed.
They went back downstairs to the poor little Pitty who was so sad to have been left alone. Good thing they weren’t gone for very long. She cuddled up to the dog again and they resumed their comedy special. It was about 10pm when it finished, and she took that as a good opportunity to bring their evening to a close. Jack saw her to the door and kissed her on the cheek as she left. It was a pleasant enough encounter. However, despite her best efforts, she knew she couldn’t force feelings that just weren’t there. She needed a guy who would challenge her, but who would also be sweet and kind – a bad boy with a heart of gold, to be so cliché.
Jack messaged her a couple times over the next week or so. She always responded, she definitely didn’t ghost him – but he eventually got the hint that she wasn’t interested in another date. He was a nice enough guy, but hooking up with him was the last straw for her.
She was sick of disappointing sex. She was sick of re-telling the same spiel to guy after guy, knowing full well they didn’t really care, just like she didn’t care about their stupid lives either. She was ambivalent towards dating now. She had said it over and over throughout the pandemic, but this time, she had really had it with online dating… (yeah, right…)