Kiss and Tell: “My Hinge date seemed normal, but he was secretly obsessed with trivia”

Welcome to Kiss and Tell, a series about the steamy, surprising and frequently absurd world of Toronto dating. Send your most memorable stories from the pursuit of love and lust in the city to submissions@torontolife.com.

—As told to Maddy Mahoney

When I matched with Scott on Hinge, I was trying to get comfortable with dating as an adult. Most of my experiences so far had been when I was in my early twenties, and they had been pretty messy. That was fun while it lasted, but I was ready to move on. Even though I was open to connecting with someone long-term, my primary goal was just getting out there and figuring out what I was looking for.

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Scott had red hair and a full beard. He was quite tall, like six foot four, and stocky, which is a body type I’m very attracted to. He dressed like the typical hipster guy you’d find in the west end: big, baggy T-shirt; plain canvas baseball cap; that sort of thing.

We chatted for a while and bonded over our jobs. He was a director for commercials, and I worked in theatre, so there was some common ground. He was funny and made a point of asking me about shows we were both watching.

We decided to meet up at a bar called the Ossington. A couple of days before our date, Scott sent me a text saying that he’d just heard the Ossington was doing trivia on the night we were planning to go. He asked whether I’d want to play or would rather meet somewhere else instead. I said I was fine to stick to our plan and that we could feel out whether we wanted to play once we were there.

After that, he asked me a bunch of questions: Did I like trivia? What subject areas was I knowledgeable in? I figured that he was just trying to keep the witty banter going. I told him I was bad at geography and history but that I was pretty on top of the pop culture stuff. In general, I’ve always felt pretty neutral about trivia, but it can be fun if you’re with the right people.

At the bar, Scott was as cute as he’d been in his photos but much shyer in person than he was over text. For the first half hour, I was really pulling teeth to make the conversation happen. He eventually got more comfortable, though, so it seemed like it had just been a weird blip. We started talking about camping and our mutual love of cottages.

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At some point, he waved over the bartender, but in this very casual way, like they were pals or something. It started to seem like Scott was a bit of a regular at the Ossington. As a former bartender, I don’t generally find it super attractive when people frequent the same bar all the time. In this case, though, I didn’t think much of it.

Then, someone came around with the trivia packages and asked if we wanted to participate. Without even looking my way, Scott reached across me and grabbed the package out of the person’s hand. He told the guy to put his name down, but he didn’t say what his name was. The trivia guy obviously knew Scott already.

It was annoying that he’d signed us up without consulting me, but it was a minor slight, all things considered. I felt like I should make fun of him for it a bit, though, to point it out. “Huh, I guess we’re playing trivia then?” I asked. “Oh, yeah, I’ve played trivia here before,” he replied. “I actually really love trivia. I play pretty often.” I asked how often. “Well,” he said, “I’d say at least three times a week.”

It turned out that Scott frequented several regular trivia nights at different bars, and it was becoming clear that the Ossington was one of them. He pointed out a table of people sitting across the bar from us. “These guys win every week,” he said. “They’re the people to beat.”

Meanwhile, he’d clearly switched into trivia mode. He was feverishly flipping through the packet. Even when he answered my questions, he didn’t look up.

It was weird that he’d lied about not knowing that this was going to be a trivia night. But I didn’t want to let it ruin the date—we’d just been having a nice conversation, plus I’d put time and energy into getting dressed. I figured it would be more work to find a way to leave than to just stay and see how it all played out.

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Once trivia started, Scott was suddenly very serious. No more laughing, no more smiles. We weren’t chatting at all anymore—he was entirely focused on thinking of potential answers. It’s like it was a life-or-death situation to him.

Each time a pop culture or music question came up, he would go from being very focused on his paper to looking at me in desperation. I got one or two of those wrong, and in those moments, I could tell that he was pissed but didn’t want to show it.

But there was one question where you had to guess what band was playing based on just the first few seconds of one of their tracks. I correctly guessed that it was the Fugees, which I used to listen to with my mom. When they announced the answer, it turned out that no one else had gotten it right. Scott jumped out of his chair and hugged me. “I knew I should’ve brought you,” he said.

We came in third, which is not bad for a two-person team—the winning team had six players. I was hoping that, once the game was over, the vibe of the date would revert back to what it had been before. No such luck. Scott started sulking. He was clearly a sore loser.

Now that trivia had ended, the bar was hosting karaoke. Earlier, Scott had suggested that we could stay and sing a bit. He knew I was a singer, so it was kind of a trade-off: some of his thing and then some of my thing. I thought maybe I could salvage the mood. But, when I suggested that we stay after all, he said he didn’t feel like it anymore. “I have to go walk my dog,” he said.

We both finished our drinks and put on our coats. As we left the bar, he asked if I wanted to walk his dog with him, but it seemed like an afterthought. I considered whether it was worth giving this guy one more chance. In the end, I said no. We gave each other a super awkward Christian side hug and left.

It took me less than half an hour to get home. As I was about to walk into my apartment, I got a long text from Scott. He wrote that he thought we’d given it a good shot but that he didn’t feel a spark. He said he appreciated the help with trivia, though. The message ended with, “Good luck out there.” I was so annoyed—there’s nothing worse than getting a condescending rejection text from someone you already never wanted to see again.

Since then, I pay a lot more attention to the things that people bring up while you’re getting to know each other. It may seem small, but I think people are pretty intentional about that sort of thing. If something like trivia comes up more than once, it may be time to cut and run.