Kiss and Tell: “I went on a date and invited my friends along to watch”

When I first met Tyler, dating had started to feel like a string of disappointments. My last date had been with a police officer who had seemed charming at first—until he told me to hold my breath when we walked past an Asian family so I “wouldn’t catch Covid.” He thought he was being funny. I left the date. Once I was safely home, I sent him a text: “Hey, I’m not interested in a second date because I really didn’t like your racist joke.” Then I blocked his number.

Most of my friends were in similar situations, perpetually stuck in a cycle of bad dates or good chats that ended with some variation on the classic “I’m not looking for anything serious.” One evening, I was hanging out at my parent’s house in Brampton with my two best friends, Zee and Simmy, when Zee came up with an intriguing proposition: “What if we all went on dates at the same time in one place...and just didn’t tell the guys?” Simmy and I were both immediately into the idea. It felt like a fun way to flip the script and turn dating into an enjoyable activity by not taking it so seriously.

We all went on Hinge and locked in dates separately for that night. The plan was to book one date at Bar A and another at Bar B shortly afterward, stacking two dates in one night. If the first date went well, we would cancel the backup. If not, we would make a polite exit and slide into date number two. The guys wouldn’t know. The only rules? Keep it quiet and sneak tequila shots in the washroom while we debriefed. Zee called ahead and told the bartender about our plan, who laughed and said, “This is iconic.” I agreed.

We all got ready at my parents’ place, debating outfits and doing our hair while passing around a bottle of wine. I was nervous—not because of the plan itself but because I’m naturally a quieter person. My friends seem to have this magnetic ease with people that I’ve always admired. I worried I might come off as cold or distant even when I was trying to be kind and attentive. But my excitement at our overall plan helped drown out the typical first date jitters.

Related: Kiss and Tell—“My podiatrist co-worker turned out to have a foot fetish”

A block from the bar, we all split up. Thank god we did—my date was early and already waiting at the entrance.

Tyler had tattoos, brown eyes, slightly tousled hair and a jean jacket with his sleeves cuffed just enough to show his ink. According to his Hinge profile, he was well-travelled, which is something I’m really attracted to. Solo travellers have this quiet bravery I envy. I’ve always wanted to do it myself but felt held back, mostly by the fears my mom passed down to me about travelling alone as a woman. I tend to gravitate toward people who have experienced the world in a way I haven’t. I just hoped he wouldn’t see my lack of travel as a red flag.

Meanwhile, my friends rolled up to the entrance and were seated one after another: one on the same floor as me and one, unfortunately, on another level of the bar.

Any time one of us needed to debrief, we’d text, “Bathroom?” and meet up to trade updates. One of my friends described her date as nice and said they were hitting it off. From across the room, I could see her laughing, and it seemed like they had no issues keeping the conversation going. The guy was tall and tan, and he wore glasses—very much her type. My other friend, who was seated on a different floor, seemed pretty bored and was more interested in what we had to say. She decided to bail and met up with her second date, so she left before me and Simmy.

I actually liked my date. It started off slow and awkward, but we soon found common ground. We’re both creative—I work in journalism, and he does graphic design and photography. The conversation was flowing so naturally that I lost track of time, and eventually I made the call to cancel on my second date.

After two trips to the bathroom, I started to feel guilty about keeping him in the dark, so I decided to come clean and told him about my best friends being close by. I even told him that I’d cancelled on my second date in order to keep spending time with him.

He laughed. “That’s actually genius,” he said. “I respect it.”

I was worried that he’d be offended or take it personally, but his easy-going response was a major green flag. We headed over to the second bar, and eventually, when my friends wrapped up their second dates, they came and sat with us, and they liked him too.

By the end of the night, we had exchanged numbers and kissed.

A few days later, we agreed to hang out again. It was freezing outside, so I invited him over for a movie night at my parents’ house. Then the vibe shifted. He didn’t seem to like my cat. He claimed not to mind, but he leaned away any time the cat came near.

Related: Kiss and Tell—“My date ordered me a salad and told me to get liposuction”

I ended up throwing on Wild Wild West, and we barely spoke through the whole thing. I even brought up our weird mutual connection—his cousin just had a baby with a friend of mine—but his responses were short. He would smile, rub his hands together like he was nervous and go back to being silent. After the movie, it was clear that our conversation wasn’t going anywhere, so I told him I was tired and that I would message him to hang out another time. We never spoke again.

Zee, Simmy and I haven’t gone on any stacked dates since. Simmy realized that she’d much rather get to know a guy first before introducing him to her friends. Zee recently became assistant general manager at a restaurant and seems too busy with work to care about dating at the moment.

I recently started dating someone new. When I told him the story about stacked dating, he laughed. “You better not have met me that way,” he joked. He thought it was clever and strategic but not something he’d ever try. “I’m a one-person kind of guy,” he said. “And I have all I need now.”

I’m glad that the dating pool isn’t as contaminated as I’d thought. You just need to do your own thing and eventually the right person will find you.