Kiss and Tell: “My girlfriend said her ex’s mom was dying. Turns out she was cheating on me”

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

After breaking up with a woman I thought I would marry, I needed to distract myself from the heartache. I took on contract work to keep myself occupied, even on some weekends. One of those gigs required taking the Yonge-University line south to King every Tuesday morning.

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On one of those commutes, I noticed a woman get on at Bloor-Yonge station. She was tall with high cheekbones, full lips and a defined jawline. Her outfit caught my eye—a long burgundy coat, beat-up black heeled boots and a New Yorker tote bag. When she got off at Dundas, I found myself wondering if I would ever see her again.

In fact, I saw her twice more over the next three weeks, both times on my way to work on a Tuesday morning. Despite the multiple opportunities, I was too shy to ask anyone out in person—let alone this intimidating, sophisticated-looking woman. I also assumed she was on her way to work and might not be in the mood to get hit on by some random guy first thing in the morning. Nevertheless, I took my attraction to her as a sign that I was ready to move on from my ex. So I downloaded Tinder.

One night, out of boredom, I asked my friend if he wanted to swipe on my behalf while I looked over his shoulder. I caught a glimpse of one profile where the woman seemed especially attractive, but I barely saw the first photo before he swiped right. I eventually revoked my friend’s privileges, but I quietly hoped that I would match with whoever that woman had been.

Over the next couple of weeks, I had dozens of Tinder conversations that went nowhere. I didn’t go on a single date. Then one day my phone buzzed. It was a notification from Tinder: “You and Leah matched!" I opened the app and checked Leah out. Sure enough, it was the woman my friend had hastily swiped right on. And, now that I could actually see her profile, I realized it was the same woman I’d been seeing on the subway.

I sent her a message: “Sorry if this is weird, but I swear I saw you on the subway a while ago. You got on at Bloor-Yonge and off at Dundas.” She didn’t think it was weird, thankfully, and said she was sometimes in that area. I decided to bring forward all my proof. I told her she’d been wearing a dark-red coat with worn-out boots and a New Yorker tote. “Wow!” she wrote. “What a memory. I guess you did see me after all.”

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We launched into a lengthy back and forth, sending hundreds of words at a time. We really started hitting it off when I expressed that I didn’t like social media. She shared the same frustrations and then started complaining about her school, which somehow led to talking shit about Marvel movies. We kept riffing. She had a great sense of humour. At one point, she said that my texting tone was reminiscent of Donald Trump. I found that bizarrely endearing.

Finally, after a couple weeks of messaging, I summoned the courage to ask her out. We met in front of the AGO and then walked to Kensington Market for coffee. But, as we approached the café, I saw my ex’s face in the window. “Keep walking,” I said. Leah was confused. “Do you see an enemy?” she asked. But she didn’t make a fuss. We walked past with our heads bowed. I didn’t dare look, but I could see Leah sneaking a peek. She told me my ex was staring at us. I started laughing at the absurdity of the whole situation, which made Leah laugh. The whole encounter made me like her even more.

We found another coffee shop and stayed until it closed. Then, having determined that we both had nothing else going on that day, we continued the date by grabbing dinner at Café Diplomatico. After that, we picked up some wine and went back to her place. I tend to take things slow on a first date, so around 4 a.m. we hugged and I grabbed an Uber home.

Over the next few weeks, we continued seeing each other. My feelings for her developed quickly because of all the time we’d spent messaging. Then she invited me to a stand-up open mic that her friend was participating in. When we met up to go to the venue together, she said, “Oh, by the way, my ex Brian is coming tonight too.” It was unexpected, but it didn’t make me uncomfortable. I assumed they were friends.

At first, it seemed like Brian wasn’t going to show—he didn’t arrive for the first two hours. When he finally got there and Leah introduced us, it was clear he was sizing me up. We shook hands, but that was it. He was very quiet for the rest of the night, and I didn’t think much of it.

Related: “My date realized I’d forgotten his name”

The next day, Leah told me that Brian was “not happy” that I had been “dropped on his head.” She seemed really pleased that Brian had been upset, like she was relishing the fact that she’d managed to irk her ex. It seemed like a red flag. Why would she still care what her ex thought if we were seeing each other? I started to wonder if she was as serious about us as I was. I felt like it might be smart for me to take a step back. I definitely wasn’t ready to get hurt again.

We took some space after that but continued dating on and off. On the good days, we were stealing ginger shots from the grocery store, watching movies and teasing each other. On the off days, she dated and slept with other men she would later make fun of—including Brian. She’d make snide comments about him, complaining that he couldn’t sit through a movie without checking his phone 50 million times. But I was still jealous.

I tried dating other people too—a law student, an architect—but I didn’t like any of them as much as Leah. Plus, I was getting tired of pretending to be chill about the openness of our relationship. So, when spring came, I asked Leah to make things official and be exclusive with me. She agreed and seemed really excited about it. We had a nice candlelit dinner at her place to celebrate.

Things seemed to be going well until, a few months later, Leah told me that Brian had reached out. She said his mother was dying of cancer and had asked to see Leah before she died. Apparently they’d gotten along super well. It felt a little odd to me, but who was I to say no to a dying woman? So Leah went, then she and Brian started hanging out one on one. Sometimes I would ask to join, but she always told me it would be awkward. It was clear something with Leah had shifted.

We finally broke up after she went on a hiking trip with her roommates and all of their boyfriends without inviting me. But we still had back-to-back appointments to get our hair cut—we had the same stylist, and for whatever reason we thought it would be a good idea to keep the appointments as they were.

We couldn’t talk much while the cuts were happening, but she stayed until I was done. After that, I asked if she wanted to get dinner together for old time’s sake. She said she already had plans with her friend Hazel.

Since we were heading in the same direction, we hopped on the subway together. As we approached Leah’s stop, she looked at me meekly. “Brian’s mom isn’t sick,” she said. “And I’m not getting dinner with Hazel. I’m seeing Brian.” Then she stepped off the train before I could respond. It was like a mic drop.

At first, I was so emotionally exhausted by the relationship that I was weirdly unfazed. But, when I had time to process my feelings more, I was devastated. I started putting together the pieces of the puzzle. I was just like, Wow, I’m so stupid. Why was I okay with her hanging out with this guy? Even now, I think I’m still too trusting of my partners. Months after the subway surprise, Leah asked if I wanted to see a movie, and I said yes. She seemed uncomfortable the whole time, and I haven’t seen her since.