“My Earls hookup turned out to have a diaper fetish”

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 Juliann Garisto

In March, my best friend Anna and I were newly single and restless. While we’d both desperately needed out of our previous relationships, the newfound independence made us feral. If we weren’t working our day jobs, we were partying until the early hours of the morning and getting ridiculously drunk. I was hardly sleeping or eating, but I was also having the time of my life.

One Saturday afternoon, my friend Michael suggested we go shopping. He had his mom’s car for the weekend. If anyone could match Anna’s and my energy, it was Michael, a gay man with the libido of a rhinoceros in heat. He picked us up from Anna’s apartment in the west end and drove us up to the Yorkdale mall blasting Charli XCX. After walking around the mall and catching up, the three of us decided to get dinner. Earls had the highest rating, so we went there and ordered some drinks and food. Then Michael said, “Fuck it, I’m ordering a pitcher; I’ll leave the car overnight.” We were cool with that plan. Soon enough, the pitcher was empty and we were ordering another.

Related: “My first date got crashed by my mom, three neighbours, two dogs and a parakeet”

Enter John, the most unassuming yet handsome man, wearing a sharp suit and carrying a briefcase. He was ridiculously hot—tall, chiselled jawline, perfectly coiffed hair. He sat alone at the bar drinking scotch, and for the next hour or so, no one joined him. My friends and I were surprised to see this man alone.

We came up with plausible backstories: he didn’t get the job, he was getting a divorce. “What do you think he’s carrying in that briefcase?” Anna asked. Michael started composing a sing-song version of Anna’s question: “What’s in the briefcase? What’s in the briefcase?” The man turned ever so slightly in his chair, and Anna had to shush Michael, whose self-awareness plummeted the moment alcohol entered his bloodstream. “What if I invite him to sit with us?” I suggested. Michael was super into that idea. Anna, on the other hand, was yawning. She’d had a late night the day before and was thinking of leaving soon. It was just shy of 9 p.m. Michael and I begged her not to go until at least ten. “Maybe he’s your future husband,” I said. Anna rolled her eyes.

Related: “My date arrived in the middle of the night and refused to leave”

I walked over from our table to the bar and introduced myself. John was a little awkward but no less attractive for it. He accepted the invitation with a shrug and joined us in our booth. Anna and Michael introduced themselves, and John shook their hands. Michael drunkenly blurted that John was super hot. Anna and I laughed, though we were also kicking Michael under the table. If John was amused by the open flattery, he didn’t have much to say about it.

I sensed an awkward silence coming and did my best to fill it with small talk. I asked John what he was doing at the Earls in the Yorkdale mall. He told us he was staying at the Hilton Hotel near the airport; he had a flight the next day to Texas, where he was from. I asked what he was doing in Toronto. “It’s just meetings,” he replied vaguely. “Yeah, but like, what company do you work for?” “What company do you work for?” he shot back, playfully but still with this stubborn resolve to remain mysterious. I couldn’t tell if he was just a business bro pretending to be more interesting than he was or if he was actually an enigma.

Anna left in an Uber not long afterward. I didn’t blame her given how dull John was turning out to be. Yet Michael and I were still down to keep hanging. There was no way he was just a pretty face, right? So after Anna left, we got another round of drinks, and Michael generously ordered each of us a shot. I knew what he was trying to do: loosen John up so we could get him to say something interesting. Unfortunately, the additional alcohol made the conversation no more eventful, and Michael and I only got sloppier.

John went to the bathroom, giving Michael and I a chance to regroup. Perhaps Anna had been right to leave early. Michael eyed John’s empty seat. “Where’s his briefcase?” I looked and noticed it too: the briefcase was gone. “I guess he took it with him to the bathroom?” I said. “Or he just straight up left,” Michael said, slightly dejected.

John hadn’t left. I saw him returning from the bathroom, head down, briefcase in hand. I told Michael, who was facing the opposite direction. It was weird that he’d taken his briefcase with him to the bathroom. We reasoned that there had to be something valuable in there.

When John sat down again, I brazenly asked if he was going to invite Michael and I to his hotel room. I was losing my inhibitions by this point, both because of the alcohol and because I was getting bored. Something had to happen now, and if it wasn’t an interesting turn in the conversation, then it was time to mobilize. John perked up in a way he hadn’t all night. “Sure,” he said.

After we paid our bills, John ordered an Uber that took us to the Hilton Airport Hotel. When we arrived, it was clear that he had money. He had a whole suite under his name and even ordered bottle service. I shot Michael a look when John handed him a glass of champagne. Michael was totally over his limit, but how was I any better? I, too, accepted the glass John handed me—even though I could hardly walk in a straight line.

This is where my memory gets a little foggy. I don’t know what Michael was doing while John and I were talking—I think I might have convinced him to go out for a smoke—but John was finally opening up. It turned out that his shroud of mystique hid nothing more than a business bro persona: he worked for Deloitte and was in Toronto meeting with clients in the auto industry, or something like that.

Eventually, and consensually, John and I started making out. Michael had passed out on the couch next to us. It was then that John asked if I wanted to see what he had in his briefcase. Here we go, I thought. He unlocked the clasp. I saw some yellow manila folders and paper with fine print and, hidden in the sleeve, an adult diaper.

“What do you think of me putting this on?” he asked.

I took a deep breath. My arousal dried and withered. I knew it was time to go. I ordered an Uber, woke Michael up and got us out of there.

People tend to think I’m insane after I tell them this story. They say, “What if the guy had pulled out a knife?” But how often do you hit on a guy only to find out that he has a diaper fetish? And besides, we were right all along. There really was something valuable inside that briefcase.