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Kiss and Tell: “I started dating my best friend’s ex. It ruined our relationship”

Mackenzie, a 31-year-old physiotherapist, was surprised to learn that everyone had their own version of events

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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


One night, I was out with some friends and swiping through Hinge. I matched with this guy named Oliver. He was tall and skinny, with dark hair, green eyes and a little diamond nose piercing. I thought he was cute, and he suggested we meet at a bar in Leslieville that night. I was already drunk, but in a way that made me feel confident in my social abilities, so I agreed. On my way to the bar, I looked more closely at the photos of Oliver on the app. He looked familiar, but I couldn’t place him.

Related: “I got married to a guy I’d known for only a few months. Then he got cold feet”

As soon as we sat down, he asked, “Are you friends with Emily?” I told him that she was one of my best friends—we’d gone to high school together. It turned out that they’d dated ten years earlier. I couldn’t remember anything about their relationship, and I didn’t want to broach the topic of exes on our first date. Instead, we talked about politics, our parents and urban planning. There wasn’t a single awkward moment, and Oliver was really good at maintaining eye contact. The time went by quickly.

He offered to walk me home, even though it was 45 minutes away, and when we got to my house, he kissed me. I invited him up to have another drink or a coffee, but he said it would be better for him to go home since it was so late. He added that he’d had a really nice time and wanted to do it again soon.

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The next day, I happened to have plans to get coffee with Emily. I told her about the date, and she immediately made a face. “Oliver? That guy’s an asshole,” she said. “He broke my heart.” I was genuinely surprised, so I asked her for the full story. They’d dated for only four months, but Emily said it was the most intense relationship she’d ever been in. They spent every single day together. She met his parents right away. She spent at least four nights a week at his place, and they both quickly said they were in love.

Then, apparently, he’d broken up with her completely out of the blue, saying he wanted to focus on his career. Emily was convinced that it was Oliver’s dad who’d persuaded him to do it. He was traditional, and she suspected he didn’t like that she was outspoken and had tattoos. She insisted that if it hadn’t been for his father, her and Oliver would still be together. I was surprised to see her get so worked up about all this, not just because Oliver had seemed nice and normal on our date but because it had been a decade ago and Emily was in a different relationship at this point.

After she told me everything, she asked me if I liked Oliver. I told her the truth: we’d just met, but so far, yes. I would go out with him again if he asked. Emily told me I shouldn’t—she said it would be best for our friendship if I never saw him again. I valued our friendship more than some one-off with a guy I barely knew, so I agreed.

When Oliver texted me later, I didn’t respond. I didn’t feel good about ghosting, but after hearing Emily’s side of the story, I was kind of put off by the whole idea. So I went on a few dates with other guys, but nothing really came from them. I started to realize that, compared to my first date with Oliver, these other ones sucked.

About a month later, I was sitting in a coffee shop when Oliver walked in. I was instantly excited to see him, which caught me off guard. He came over to my table right away. After about twenty minutes of catching up, he asked why I’d never replied to his text. I said that I’d wanted to, but that certain obligations had gotten in the way. Immediately he was like, “Emily said something, didn’t she?”

Related: “I saw my friend’s boyfriend on Tinder. We decided to ambush him”

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I’m not one to avoid the truth, so I admitted that it was because of Emily. He sighed. He told me he wasn’t proud of ending their relationship so abruptly. “So why did you break up with her?” I asked. He said that, after going away for a weekend with some friends, he’d realized that their relationship was unhealthy and codependent. “While I was away,” he said, “she was texting me every second. If I didn’t respond within the hour, she’d accuse me of not loving her.” So, when he got back, he ended it. She was devastated and angry, and she continued texting and calling him constantly. One day, he had to tell her quite aggressively that they would never have a friendship if she kept pressing him.

I believed he was telling the truth, especially because he admitted to handling some of it poorly. “Did she tell you what happened after that?” he asked. Apparently, after he’d refused to maintain contact, she’d proceeded to date one of his best friends. My jaw dropped. How could she omit that detail from her side of the story? I felt annoyed and confused. Did she still have feelings for him after all these years?

Oliver and I agreed that running into each other meant the universe was trying to tell us something. “Perhaps,” he said, “the message is: we should go on another date.” I was flattered and couldn’t ignore my excitement, so I agreed. We went for dinner that weekend. It felt natural and easy to be in his company. I didn’t tell Emily about it.

Things with Oliver continued to progress, and after three or four months, it felt pretty serious. I figured it was time to tell Emily. We made plans to grab a drink. She asked me how my dating life had been going, whether I’d met anyone promising on Hinge. I told her that, a few months ago, Oliver and I had bumped into each other and ended up talking and hanging out for most of the day.

“What did you guys talk about?” she asked. I told her everything. “He said he was sorry for how things ended with you two,” I said. “But he also said that you went and dated his best friend afterward.” Emily rolled her eyes at this. “I can’t believe he isn’t over that,” she said. I thought that was ironic. “We’ve continued to see each other,” I said, “and things are getting pretty serious.” Emily looked incredulous. She said she was angry because I’d kept it hidden from her, but a part of me knew this wasn’t the truth. If she’d really let go of her past grievances, she’d be happy for me. The rest of the night was awkward. She left soon afterward, saying she had to be up early the next morning. I knew that was a lie—she worked from home and set her own hours.

Related: “After my date, I had to get my tampon removed in the ER”

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I tried to look past her reaction and maintain our friendship, but it was hard. It made me question the foundation of our relationship. Had I really been friends with someone so immature all this time? I was afraid to bring Oliver up in conversation when I was with her, and I could never bring him along to group hangs. If he did happen to get mentioned, she would tell me that it wasn’t going to last, that he would only break my heart like he did hers. It was really hurtful. We started texting less, and we rarely hung out one on one.

Then, one night at a friend’s birthday party, I got a little drunk. I confronted Emily about the differences between her and Oliver’s sides of their story. It was a childish impulse, but I went through with it anyway. I brought up the fact that she’d low-key harassed Oliver, dated his best friend and then kept all that hidden from me. Emily denied that she’d been needy and claimed that the move she’d pulled on his friend (which had turned into a one-month fling) was her last attempt to get Oliver to realize he’d made a mistake by breaking up with her. At that point, I knew we wouldn’t be able to stay friends. She had her narrative, and I had mine.

These days, we see each other only at parties or hangouts with mutual friends. We’re civil, but mostly we avoid each other. Oliver and I are still together—we just celebrated our one-year anniversary. I do miss Emily, though. I hope that one day she can move on, for everyone’s sake.

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