Kiss and Tell: “I started sleeping with my roommmate. Then he fell in love with someone else”

Kiss and Tell: “I started sleeping with my roommmate. Then he fell in love with someone else”

Leigh, a 23-year-old social worker, learned the hard way why “no hooking up” is the cardinal roommate rule

An oven mitt and spoon on top of a background of blue hearts

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


When I met Trevor, I had just gotten out of a long-term relationship. My ex and I had been living together, and when we broke up, we agreed that she would keep the apartment. Basically, I needed to move out as soon as possible.

Related: “My date got a fish bone stuck in his teeth. He insisted on calling 911”

I came across an ad on Kijiji for a room in a four-bedroom house in the east end. It was three storeys tall, with two bathrooms, a giant backyard and a private balcony. It was well within my budget, and the room being advertised was on the top floor—a big improvement from my previous basement spot. It seemed perfect, but the only caveat was that the three other tenants were men. Since I’d only ever lived with women, it made me a little nervous.

I put in a request for a viewing so I could suss out the situation. The house was as good in person as it was in the photos. All the common areas were furnished: the living room couch looked new, and there was a giant TV mounted on the opposite wall. There was also a sunroom, a den, and in the backyard, an herb garden and a hammock underneath a weeping willow. Damn, I thought, these dudes actually have good taste. After seeing everything, I was pretty set on living in the house. I just needed to make sure I got along with the other tenants.

After some back-and-forth with the landlord, I met the three guys. They were all super friendly. Two of them worked for the same tech company, where they were in the office full time. The other one, Trevor, and I both worked hybrid jobs and would be home more often. We all got along right away, so I signed the lease that day and moved in the following week.

My ex and I were still on good terms, so she offered to help me move. Trevor was the only one there when we arrived. He saw us pull into the driveway, came out to help us unpack and ended up carrying most of my stuff into the house. I thought he was super polite and attentive. When he went back inside, my ex turned to me and said, “He wants to sleep with you.”

I was confused—I hadn’t noticed him flirting or anything. Then I was annoyed, because getting romantically involved with anyone at that time, let alone one of my new roommates, was not the plan. I asked my ex what made her think he was into me. She said he had stared at me the whole time we were unpacking. “Not true,” I said.

But, in the weeks after I moved in, sexual tension did start to build between me and Trevor. It turned out that we had a lot in common. We were both vegetarians who cared about the environment, and we were both obsessed with Bombay Bicycle Club. Plus we loved coffee. We’d drink cup after cup in the mornings when we were working from home. It didn’t hurt that he was undeniably handsome. He had brown hair, blue eyes and a really nice smile.

Our mutual attraction was hard to ignore, especially because Trevor often made really intense eye contact. It never made me uncomfortable—it actually made me excited. I started to crave being around him. If he happened to come into the kitchen while I was making breakfast, I got butterflies in my stomach. If he left one of the bathrooms right as I was about to try the door, I was destroyed.

It definitely complicated my living situation. Not only was I adjusting to a new home but I was crushing hard on one of my roommates, which made me second-guess every decision about my clothes, hair, makeup and even how I went about my day. I talked about it to some friends. They reassured me that, if things went south, I could just move out. It sounded like a simple getaway plan.

At first, it seemed like Trevor and I had an unspoken agreement to respect the cardinal rule of platonic cohabitation: not to cross the point of no return. In reality, it was only a matter of time before one of us made a move.

One night, after I’d been living there for about a month, our other roommates were both out at a work event. Trevor and I decided to watch a movie. It was the first time we’d officially made plans, and I wondered if this would count as our first date. Then I wondered if I’d been imagining the whole thing. Basically, I was nervous.

Related: “I tried to break up with my boyfriend, but his dad wouldn’t let me”

Sure enough, twenty minutes into the movie, we leaned in at exactly the same time. Suddenly we were making out, then taking our clothes off, then he was carrying me up to his room. It was the hottest sex I’d ever had. Afterward, I honestly thought I might be in love.

Going forward, we tried to keep things discreet. We didn’t talk about what we were to each other, but we continued to hook up. Often, it was during the day, when everyone else was at work. But there were a couple of nights when I slept in Trevor’s bed. We had to be extra quiet those times since one of the other bedrooms was right next door. Even though I felt like I might have serious feelings for Trevor, I liked that our relationship status was ambiguous. I didn’t feel emotionally ready for anything official.

Then, one Saturday morning, one of the other guys in the house popped the question that was on everyone’s mind. “Are you guys dating or what?” he asked. I felt myself blush. “Or what,” Trevor answered. Our other roommate came back with, “If you’re not dating, then I dare you to download Hinge.” Trevor hated dating apps, but I guess he was hell-bent on denying the allegations against us. He downloaded it on the spot, and we all helped him make his profile. I thought it was hilarious. It was better than him admitting to our recent shenanigans and making everyone feel awkward.

Later that week, I noticed Trevor acting differently toward me. He didn’t seem as interested. He was still super nice and polite, but he spent more time in his room and didn’t actively seek me out. I asked him if everything was okay, and he said he was just super busy with work. I started to feel a little hurt, so I focused more on my work and tried to get out of the apartment by spending time with friends.

One night, I was in the living room when he came home around 11 p.m. I casually asked where he’d gone, and he told me flat out that he’d been on a date. That didn’t bother me so much, but it did take me by surprise. It was what he said next that hurt the most: “I think I might be in love.” I was shocked by how terrible it felt to hear that.

He told me more about the woman he’d been out with, how she danced for the National Ballet and was apparently very talented. Then he showed me pictures of her. Damn, I thought, she looks like a model. I knew right then that whatever had been going on between us was over.

Over the next few weeks, I realized why people warn against dating your roommates. I had to watch Trevor cook this woman elaborate candlelit dinners. Then I saw her sitting next to him on the couch, where we’d kissed not that long ago. I even heard them having sex. I started spending a lot of my time alone in my room. I was trying not to think about the situation, but obviously that was difficult when it was happening in my home. I seriously considered moving out. I browsed listings online, but none of them were as nice as my current place. I even considered moving back in with my ex, but that just felt regressive.

I finally decided to confront Trevor about it. It felt like the only way to regain some sense of dignity. So I pulled him aside and said, “Look, I’m really happy you’re in love, but it kind of sucks that you left our relationship undefined and then randomly started seeing someone else.” He was extremely apologetic. I was still pissed that he hadn’t thought about the consequences of his actions, but I could tell he felt terrible. “Do you want to move out?” he asked. “No!” I replied. “I love this apartment.”

The conversation helped. Trevor admitted to taking me for granted and assuming that I’d rather just “let things be” than talk about it. He said he’d been as surprised as I was that he met this woman and instantly developed feelings for her. Afterward, we hugged and went our separate ways on good terms.

Eventually, I even became friends with his Hinge date, who is now officially Trevor’s girlfriend. Sometimes, all five of us hang out, or just me and her will chat in the kitchen. It doesn’t feel weird at all, and I actually really like her. I’m happy for them both.