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Kiss and Tell: “My date took me to a casino and ditched me to play slots with her aunts”

Sam, a 27-year-old artist, was looking forward to some alone time with his crush. Instead, he inadvertently went on a day-long trip to visit her extended family

Kiss and Tell: “My date took me to a casino and ditched me to play slots with her aunts”

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 .

—As told to Juliann Garisto


When I went out with Steph, I was living in Oshawa with my mom and older brother. I was trying to get work in film but didn’t have much else going on. I was hanging out a lot with my friend Lauren, whom I knew from high school. We were basically talking every day, and Lauren had this best friend named Steph, whom I had a crush on. Steph was very pretty: long dark hair, striking eyes. She was an aspiring actor and had a lovely singing voice, which I found very attractive. The three of us would hang out or go to house parties together, and Steph and I would often end up flirting. Sometimes it would be touchy, like if we were sitting on a couch, she’d sit extra close to me. Other times, we’d just talk.

I could never get a full read on how she felt, but it definitely seemed like there was a spark. I never quite got up the nerve to asked Steph out officially, though. And Steph had suggested that Lauren had a crush on me even though Lauren was encouraging me to ask Steph out. The dynamic was a little complicated, which made me nervous.

But then, one night, Lauren had a house party, and Steph and I drunkenly made out in the bathroom. A few days afterward, she told me she had an upcoming doctor’s appointment in Toronto. Then she asked, “Do you want to come with me and we can hang out after?” It wasn’t entirely clear whether it was meant to be a date, but I figured that, since we’d recently made out, there had to be some romantic intentions. So I said yes.

On the day, she drove us into the city, then I sat in the waiting room at her doctor’s office while she went in. She hadn’t told me how long the appointment would take, so I just flipped through a magazine and checked my phone. After about forty-five minutes, she emerged. Great, I thought, now we can actually spend some time together.

I was on the verge of asking where she wanted to go next when she said, “I have to stop in at my family restaurant.” I was like, Family restaurant? Where? It turned out that her family owned an Italian restaurant in North York. I thought, Okay, we’ll get this over with and then we’ll be able to hang out.

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When we walked into the place, I was immediately struck by how tacky it was. The walls and ceiling were painted salmon pink and had white moulding accents with dramatic flourishes. There were separate dining areas, all different sizes, connected by square archways framed with kitschy Roman pillars. The table settings were excessive—red linen napkins, two types of wine glasses, three sets of cutlery, and plates of pre-packaged butter and sugar. I wondered if there was some sort of event happening, but the dining room was empty and dead quiet. There was one group of intimidatingly large men who sat at a table near the bar, chain-smoking cigarettes and drinking espresso. These were, I learned later, Steph’s uncles. I felt like I was in a scene from The Godfather.

There was no formal introduction. Steph just told her uncles my name, and they nodded. I wasn’t expecting anything, but it would have been nice if they’d offered me a glass of water or some bread, which they didn’t. They did have a lot of questions about my intentions toward their niece, though. “Are you a nice guy?” Yes. “What do you do for a living?” I work at Old Navy. One uncle with permanent frown lines and a goatee said, “You’re not Greek, are you?” No. “Good, ‘cause I’d have to kill you if you were Greek.” I thought it was a joke, so I laughed, but no one else did. It felt like they were looking me up and down the whole time, as if to say, Who are you?

We were only there for about ten or fifteen minutes, but it seemed like an hour. I felt trapped—it would be rude for me to suggest that we leave in front of everyone. When that wrapped up, I thought we might finally be getting somewhere. But then Steph said, “Oh, by the way, we have to go meet my aunts at Wimpy’s.” Great. So off to Wimpy’s Diner we went.

Even at this point, I still had some vague hope that we’d eventually get to be alone. In the meantime, we arrived at Wimpy’s and found her two aunts sitting in a booth near the entrance. One aunt was brunette, sullen and pouty; the other was blonde, bubbly and smiled a lot. I ordered a plate of spaghetti while tuning out most of the conversation, which was pretty bland. They never spoke directly to me anyway. The sullen aunt talked about family drama and her new electric toothbrush while the other aunt smiled and nodded along.

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Occasionally, Steph would give me these repentant looks, as if to say, I’m sorry about all this. I was ready to forget about the whole ordeal if our proper date started soon, but I wasn’t so lucky. Somehow, the topic of going to the casino came up. Steph’s aunts wanted to go, and they wanted Steph to drive them. She agreed. Oh my god, I thought, this is never-ending.

When we got back into the car, I was demoted to the backseat while the meaner-looking aunt sat in the front next to Steph. At that moment, I realized we’d probably never get around to going on our “date.” I really wanted to go home, but since I didn’t have my driver’s licence, not to mention my own car, that didn’t seem like an option.

When we arrived at the casino, the flashing lights and crowds of ominous-looking strangers made me immediately uncomfortable. I’d never been to a casino before, but Steph and her aunts seemed familiar with the place. They started playing the slot machines while I tried to get a moment alone with Steph. Since Steph was fully occupied by her aunts, I decided to try one of the machines for myself. I lost five dollars.

I realized that the only way out of the situation was to get someone else to come pick me up. I didn’t want to offend Steph or her aunts, so I cheerfully suggested, in front of them all, “Hey, why don’t we invite Lauren to join us?” Lauren drove over, and thankfully I managed to get to her before Steph did. I told her about the saga of weird family encounters and said I needed her to get me the hell out of there. She thought that the whole thing was pretty funny, and then we said goodbye to everyone and quickly left, without giving much of an explanation. It was definitely a bit awkward for Steph—Lauren had only just arrived and suddenly we were leaving together. But the aunts were the nicest they had been the whole afternoon once they realized it was time for me to go.

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Steph and I never went on another date after that—she never asked, and I didn’t feel obliged to ask either. We had never even hung out one-on-one. For a while, if we happened to be at the same party, we’d talk and maybe make out a little, but it never went beyond that. Eventually, I started seeing someone new and stopped talking to Steph entirely. Moving forward, I definitely try to know exactly what kind of situation I’m getting into beforehand. Better yet, I plan the date myself.

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