Kiss and Tell: “My summer fling paid for expensive vacations and nights out. Then he started tracking my location”

Olivia, a 23-year-old student, overlooked a few red flags in favour of free tickets to Raptors games and concerts. But the situation soon took a turn for the worse

Kiss and Tell: “My summer fling paid for expensive vacations and nights out. Then he started tracking my location”

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 Tara DeBoer

It was early summer when I started chatting with Kyle. I’d just ended my relationship with my piece-of-crap boyfriend, so I was newly single. I was in my party-girl era, when I was focused on seeing people casually and having fun in the city.

So, when I posted a photo of myself to Instagram during a vacation in Nova Scotia and saw that a random guy from Toronto had liked it, I was intrigued. Shortly afterward, he slid into my DMs with a cheesy pickup line: I hope you’ll be back in town long enough to meet up one day. I didn’t know him, but I noticed that we had some mutual friends. Over the next two weeks, he’d reply to my stories here and there, but nothing consistent. He wasn’t bad looking—big brown eyes, straight brown hair and a fit body. Based on his profile, it looked like he travelled and partied a lot, so he must have had money. I thought, Why not?

When I was back in Toronto, I agreed to meet him. It was a Thursday, and I vowed that it would just be one drink; I had to get up early for work the next day. We met at a bar, and he was immediately very easy to talk to. There were no awkward breaks in our conversation. I ended up breaking my promise to myself—we decided to share a massive alcoholic punch bowl, and he ordered us shots at the bar. Needless to say, we both got drunk. I could tell he was spontaneous by the way he talked about his travels, which included lavish vacations to Italy and rowdy weekends in Miami. He also bragged about spending his money on luxuries like bottle service and VIP booths—even though he said he was a student with no job.

He mentioned that he was going to New York that Saturday, and I jokingly said I’d join him. A few minutes later, he turned his phone around to face me—he had booked us two round-trip tickets. The flight was in two days. I was shocked but also drunk, so I agreed to go. I’d never done anything like that before. I wasn’t thinking anything like What if he’s a serial killer? I was so naïve, and I just felt like being wild. That night, he kissed me on the sidewalk outside the bar. He was much shorter than me, so it was pretty awkward. I think it was the first and last time we kissed standing up.

The morning of the flight, he picked me up at 5 a.m. During the drive, I could tell that we were both excited but also super nervous. Neither of us was exactly sure what we’d gotten ourselves into. When we got to the Big Apple, it was scorching hot. We probably walked 20,000 steps, hitting all the tourist spots: Rockefeller Centre, Central Park, different street markets. He paid for everything. We finished off the night with Chick-fil-A at the hotel, exhausted from the day. It was fun. We still weren’t totally comfortable together, so the conversation was pretty superficial—commenting on interesting people and buildings we walked past or the weather. But, in general, we had a good vibe going. Were we soulmates? No. But that wasn’t my expectation. I just wanted to have fun in New York.


On the way home, there was a mix-up at the airport, and it turned out that we didn’t have seats booked. Kyle went over to the desk to handle it and soon returned, explaining he’d worked his magic by telling the attendants that his dad was a wealthy frequent flyer on the airline. It seemed odd, but I didn’t question it. I was glad that we were getting on the flight.

After that trip, we spent the summer going to concerts, Raptors games and VIP events downtown, where we’d get top-notch treatment. I hardly paid for a thing the whole time. I just assumed that he was spending his rich dad’s money. To be honest, something seemed off, but I couldn’t really put my finger on it. So I put blinders on and decided to not worry. I’d pay for a drink here and there, but he always quickly whipped out his card to grab the bill and never asked me to pay him back. It was an unspoken understanding.

I still had no intention of dating him seriously, but as time progressed, it was clear that he wanted to be in a relationship. Whenever I’d start to object to full-on commitment or attempt to turn him down for dates, he’d dangle upcoming events that we were planning to attend in my face, making me feel bad for leaving him hanging. So I kept seeing him.

After a few months, he started to call me four or five nights a week, drunk. He’d confess his feelings for me and ask me to commit to a relationship. He became very possessive, always holding my hand and making sure I was within reach at social gatherings. One time, he showed up to a party I was at with my friends, one that I hadn’t invited him to. Another time, he got kicked out of a bar we were at for being too drunk and tried to climb his way back in multiple times. It wasn’t cute.


It also became clear that some things about him weren’t quite adding up. He had four or five different credit cards in his wallet, which seemed shady to me. He also claimed that he was a student, but I saw no proof of him going to classes or doing schoolwork. I started to feel like I didn’t want to see him anymore, but I was scared to act on it because he was so obsessed with me.

By this point, summer had ended. My friends and family started to mention his red flags. They were clearly concerned. When a friend of mine jokingly told me that she wouldn’t be surprised if he was tracking my location, I checked, just in case. Sure enough, I discovered that my location was being shared with him at all times, something he must have secretly enabled on my phone. I freaked out. I knew I needed to get out of the situation.

I was too scared to confront him about tracking me, so instead I slowly started to distance myself. Since he was so pushy any time I rejected him, I felt like the only way out was to wean him off of me. I started being short over text and ignoring his FaceTime calls. Eventually, after being repeatedly rejected, he got the hint and stopped asking me out. After a few months, I saw him on social media doing the exact same thing with a series of new girls—taking them on expensive outings, presumably paying for everything. I worry for them a bit, but despite the bad vibes toward the end, I don’t think he’s dangerous. To this day, he’ll still reply to my posts here and there. Nothing insane, thankfully.

I have no regrets. In the moment, I was leaning in to the beauty of being young and naïve. I didn’t really care about the potential consequences; they never even crossed my mind. I do wish I hadn’t let it drag on as long as I did, and I feel like all the partying aged me ten years. It was fun while it lasted, and I got it out of my system—I have no desire to do something like that ever again.


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