Kiss and Tell: “My Tinder date brought me along as she met her biological family for the first time”

Welcome to Kiss and Tell, a new 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 [email protected].

—As told to Rachel DeGasperis

When I matched with Emily on Tinder, I was bored and lonely; most of my friends had left town for the summer. So I did what any horny young person does: I began swiping. Emily was from the Niagara region but was visiting Toronto with some friends for the day, and she invited me to meet up with them on Yonge. When I walked up, the first thing I noticed about Emily was her long straight dark-brown hair, which hit her waist. She was more relaxed and reserved than her friends, who were boisterous and generally didn’t pay much attention to me. It could have been awkward, but Emily was super friendly and acted as if I were a regular part of their group.

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In that area of the city, there isn’t much to do but browse the corny tourist shops filled with “I heart Toronto” T-shirts. After two hours, Emily said she was bored and invited me back to her house. Even though she lived pretty far away, I told her I was down. She was cute, kind and easy-going, plus I was desperate for an adventure. I thought, Why not see where this goes?

We arrived in Niagara Falls in record time—only 45 minutes—because Emily was going 150 kilometres per hour on the highway. We dropped off one of her friends, Ashley, whose girlfriend was waiting for her on the lawn. They immediately broke into an incoherent screaming match. Before I could figure out why they were fighting, Emily said, “This is crazy,” rolled up the windows and quickly backed out of the driveway.

From there, we drove to tourist destination after tourist destination and spent most of the day wandering around the neon-lit streets and popping into cheesy restaurants. Emily was really funny—I laughed the whole time as she told stories about what she was like in high school. On the way home, she insisted on stopping at a random bar off the highway to have a few drinks. “I love pornstar shots,” she said.

I was tipsy by the time we arrived at her house, and it was only then that I realized I’d made a grave mistake. The place was filthy. There were piles upon piles of magazines, clothing and other random objects scattered around, and it smelled musty—it clearly hadn’t been cleaned in a long time. I immediately wanted to leave, but I was a long way from home without a car of my own.

Luckily, Emily had mentioned that she owned an RV, so I casually suggested that it would be a fun adventure to camp there for the night. It had the added bonus of giving us more separation from her parents, whom she lived with, so she agreed. We got into bed: a mattress with no sheets. I spent the night trying to ignore the smell of dust.

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The next morning, I was antsy to get home. Emily drove me back to Toronto, and when I realized that my parents weren’t home, I asked if she wanted to stay a bit longer. She had been unfailingly generous during our time together; I would have felt guilty asking her to leave right away. So we decided to watch Titanic. We cuddled during the movie, and Emily began telling me that she was adopted and barely knew her biological family. The day before, she’d messaged her birth mother, who lived in Toronto, to see if she wanted to reconnect.

Lo and behold, Emily suddenly got a text. Her body stiffened, and she started typing frantically. It was her biological mom. “Hey, are you still in town?” it read. “I’d love to take you out for dinner and catch up.” She seemed nervous, which was fair enough—she knew almost nothing about the woman. Eventually, she asked me if I could go with her as a buffer. We were approaching 24 hours together, and at this point, I wanted the date to be over. But I felt like I was already in too deep, so I said yes.

We drove to a steakhouse in an Etobicoke strip mall. Emily’s mother had dyed black hair and a raspy voice. Like Emily, she wore flip-flops. I was introduced as a friend, and I watched silently as the two gushed over each other and caught up on decades of major life events.

About halfway through dinner, her mom told us that she owned the sex shop next door and asked if we wanted to stop by and take a look. Emily was excited about the idea, and I was genuinely curious. So, after the bills were paid, we walked over. The store had white walls and white tile floors under bright fluorescent lights. In the centre of the room, there was a circular counter filled with condoms and dick-shaped lollipops.

While her mom showed us her sex toys, I mentioned that I had never owned a vibrator. Her mother replied that she would be thrilled to gift me my first one and handed me a black number with jewels around the base. Just as we were about to leave and I started to think this whole ordeal might be coming to a close, her mother exclaimed, “Oh my god! I almost forgot—there’s a small family gathering at your grandmother’s house this evening. Would you two like to come?” Emily quickly responded, “Yes!”

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I had no clue where I was and wasn’t sure how to get home, so I had no choice but to pray that the visit would be quick. When we arrived at the house, the aunts and uncles swarmed Emily, teary-eyed over the years they’d missed and overjoyed by the opportunity to catch up. Recognizing my place as the awkward intruder, I meandered out to the backyard. There, I found a massive cannabis garden with plants taller than me.

The family eventually migrated out there too, and her uncle asked if I wanted to smoke with him. I needed something to take the edge off, so I followed him into the basement. It was unfurnished, with raw wood and exposed beams. He led me into a small room that was wrapped in plastic from floor to ceiling. I started to panic. Holy shit, I thought, I’m about to get murdered.

But then his girlfriend came in carrying a dab rig, which is like a massive, metre-tall bong. I had never smoked out of one before, so I didn’t realize how concentrated it was. I took several massive puffs and got belligerently high. When we went back upstairs, my mind began to swirl. Where am I? Why am I at this family reunion? People were crying and flipping through photo albums. Thankfully, Emily’s grandmother took one look at me and said, “I know what you need.” She handed me a huge bowl of mint chocolate chip ice cream. For the rest of the night, I shovelled ice cream into my mouth while everyone else discussed their family lore.

When we were finally leaving, her grandmother rushed out to the car to hand me a baby weed plant as a gift. The date ended with us hurtling back to Toronto as night fell, and I—plant in lap, high out of my mind—felt paranoid about the prospect of running into cops.

That should have been the last time I saw Emily. But, as it turned out, I’d forgotten my keys in her car. I met up with her again several days later on the sidewalk outside my home. I’d been less responsive to Emily’s messages in the days after our date, so the exchange was awkward. I was drained of energy, still over-stimulated from the two days we spent together. I don’t regret it though. It’s just a testament to the perils of having too much time on your hands.