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Kiss and Tell: “I saw my friend’s boyfriend on Tinder. We decided to ambush him”

Isabella, a 29-year-old freelancer, spent weeks laying the groundwork for their revenge

Kiss and Tell: "I saw my friend's boyfriend on Tinder. We decided to ambush him"

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 .

—As told to Juliann Garisto


I downloaded Tinder for the first time while I was in the drama program at my university. Like every other horny and curious 20-something, I became obsessed with swiping. Deciding who was and wasn’t attractive was a soothing remedy for having been rejected by men in the past, plus it was just plain addictive. For a while, it was all my friends and I talked about. I was looking for casual flings with hot guys, though I didn’t go on many dates. The guys I was attracted to were mostly unresponsive. Only creepy men seemed to like me.

One of our classes was in a room with a TV mounted on the wall, and you could connect your phone or laptop and share your screen with everyone. We would take turns connecting our phones during class. While the lead actors ran their lines over and over, the rest of us scrolled through our personal Tinder feeds, collectively judging every male specimen who happened to cross our radar. We were pretty mean at times—too mean to repeat here—but sometimes, a cute guy would pop up and one of our single classmates would ask whoever was currently scrolling to swipe right on her behalf. It was extremely entertaining.

One day, my phone was connected. I had been swiping left on every single guy until I came across someone I recognized and gasped. It was Mark, who was supposed to be dating my roommate’s friend, Maria. Maria had shown us a bunch of photos of him. When my classmates saw my reaction, they immediately started asking questions: What’s wrong? Who is he? So I told them, and their jaws dropped.

Mark was a small gremlin-like man with big, beady eyes and curly brown hair. He was fit but scrawny. One of my friends said I should play a little game with him. “You think I should swipe right?” I asked. Everyone said yes—they were basically cheering for me to do it. For the first time, we almost got in trouble for disrupting the class.

I swiped right, and it was an instant match. As the early-2000s graphic popped up on the screen, we were doing everything we could to stifle our laughter. “Message him! Message him!” my classmates said. So I typed out, “Hey,” followed by a smiley face. He immediately messaged back, “Hey, you’re cute.” Everyone was in hysterics. I knew I’d started something that I’d now have to finish.

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Later that day, I told my roommate and Maria about my discovery. They were as shocked as I’d been. Mark had spontaneously bought Maria flowers not that long ago. But, considering they’d been dating for only a few weeks and had no prior history—they’d met at a bar—it really wasn’t all that surprising. He was basically a stranger.

Maria was pretty upset when she found out. She locked herself in her room for a couple of hours. When she finally came out, she had a small suitcase and plans to stay with her parents in the suburbs for a week. She wasn’t angry at us, but she was fully prepared to seek revenge. “Let’s fuck with him,” she said. “I just don’t need to be around for it.”

That night, I created a group chat with Maria, our roommate and three of my friends from drama class so that we could devise a plan. It quickly became a vigilante-justice kind of thing. Admittedly, it was a little cultish and cruel, the way we egged one another on and felt we were right to humiliate him. We immediately ruled out blackmail: we could get arrested for that sort of thing, probably. We landed on the idea of luring him out into a public setting where the six of us could confront him.

The first step was to get close to Mark. For two weeks, I kept up a consistent back and forth with him. We even spoke on the phone a couple of times. He was very sexually forward from the get-go. He sent me nudes and described, in vivid detail, the things he would do to my body if we met in person. It was low-key gross. However, I could see why Maria had fallen for him. He was smart and a good conversationalist. He knew just what to say in every moment, and he struck a good balance with his response rate—he wasn’t overbearing or needy, but he also wasn’t distant or detached.

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We talked about all sorts of things: our jobs, where we’d grown up, what we liked to do in our spare time. Looming in all of our conversations was this one-sided sexual tension. He was apparently really into me, and I was managing to convince him that I was genuinely interested in him as well. I didn’t mind the attention, but I definitely wasn’t attracted to him. All the while, he was continuing to text Maria, who was playing along like she knew nothing. Since she’d gone to stay with her parents, she had an actual excuse to give when Mark asked her out. Still, he would send her heart emojis, call her “baby” and say things like, “I miss you.” We collectively cringed in our group chat as Maria relayed every interaction.

Finally, Mark and I arranged to go on a date. He kept asking me to come over to his place, which I obviously wasn’t down for. Instead, I suggested that we meet at a bar, and he agreed. We were all planning to be there waiting for him when he came in, with Maria front and centre. We started perversely looking forward to it.

I met the rest of the group at the bar a little early. We set ourselves up so that, when Mark entered, he’d see me sitting in a booth by myself while everyone else waited behind the curtain that led to the bathrooms. It was exciting. No one was nervous—he was seriously outnumbered. In the lead-up, we drank quite a bit of tequila.

When Mark finally came in, I smiled and waved him over. Then, from behind a curtain, I heard Maria call out, “Hi, Mark, are you having fun?” She came out, with the other girls parroting Maria’s “Hi, Mark!” over and over.

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He was stunned. Then he frowned and asked what the hell was going on—who were these random women? “What are you doing here?” he asked Maria. She said she knew that he was dating other women. Then she called him a two-faced piece of garbage. He got really defensive. He shouted, “I never did anything!” But it sounded so whiny that we all started laughing. Mark was pretty pissed.

Maria started reading out texts he’d sent her while talking to me, then I did the same. I told him that he should be ashamed of himself for thinking he could get away with being a liar. Maria’s friend, my roommate, told him that trying to cover it up was even more disgraceful. “What would your mother say?” I asked. We were pretty drunk by this point; I almost started feeling bad. Maybe, if he’d actually shown remorse, I would have regretted it. But he had so much pride and wouldn’t admit he’d done anything wrong. So I made some rude comments about his penis, and Maria broke up with him on the spot. He freaked out, threw a last few insults and stormed off. I was practically shaking—I’d never had such an intense confrontation before. It wasn’t a great feeling, to be honest, but now that it was all over, we could finally relax.

For the rest of the night, we continued drinking and cursing Mark and his faithless, two-faced, fuckboy ilk. We told Maria that she deserved so much better: she was so much hotter than Mark, and she’d dodged a bullet. And none of us ever saw Mark again—thank god.

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