Toronto Life’s most-read Kiss and Tells of 2024
This year’s worst romantic encounters include ER trips, elaborate lies and hasty marriages
Some truths are eternal, regardless of the year. The fact that this city’s dating scene can be a bizarre, hellish place is one of those truths. And yet, Torontonians in pursuit of love and lust have little option but to brave it, red flags and all. Luckily for us, some of them opted to spill all the details in our dating series, Kiss and Tell. This year, would-be lovers were thwarted by tampons, fishbones and salads—here’s wishing them better luck in 2025.
Here, our readers’ favourite dating stories from 2024.
No. 10 “My date ordered me a salad and told me to get liposuction”
Lora, a 46-year-old educational assistant, was willing to overlook Stefan’s Fox News addiction and the fact that he didn’t support gay rights. But, when he unexpectedly brought his son along for their date and then ordered on her behalf, she’d had enough. | As told to Andrea Yu | June 18
No. 9 “My Tinder match cold-called and kept me on the phone for four hours”
Demetra, a 23-year-old student, didn’t manage to escape their initial call until after her date insisted on singing her a lullaby. Opting to ignore the strangeness, Demetra went out with her anyway—but the last straw came when she started doing push-ups on the subway. | As told to Juliann Garisto | May 9
No. 8 “My date got a fish bone stuck in his teeth. He insisted on calling 911”
Gigi, a 32-year-old design consultant, refused to reach inside his mouth to get it out, and he insisted that tweezers and dental floss were a no-go. In the end, there was no preventing an unnecessary visit from the paramedics. Oh, and did we mention it was New Year’s Eve? | As told to Kirsten Fee | April 10
No. 7 “The first time I had sex was on a cruise ship—and my date’s grandma walked in on us”
It seemed like the perfect scenario for Noah, a writer, to have his first sexual encounter—empty hotel room, no parents, cute girl. That is, until he was scrambling to get dressed on the deck because his date’s grandma came back unexpectedly. | As told to Juliann Garisto | March 21
No. 6 “I started dating my best friend’s ex. It ruined our relationship”
After a fantastic first date with Oliver, Mackenzie, a 31-year-old physiotherapist, found out he had dated her best friend. Their breakup had been contentious, but Mackenzie thought they could all work it out—big mistake. | As told to Juliann Garisto | June 14
No. 5 “I hooked up with a stranger at his stepmom’s birthday party, but his relatives kept walking in on us”
Ada, a 29-year-old costume designer, crashed a house party hosted by a family she’d never met. She started hooking up with Mark, who lived in his parents’ basement, but they were interrupted by his aunt, who walked in while he was buck naked. | As told to Juliann Garisto | April 24
No. 4 “My girlfriend said her ex’s mom was dying. Turns out she was cheating on me”
Leah repeatedly assured Erik, a 28-year-old film producer, that her ex-boyfriend was not a threat. It’s just that his mom was dying and he needed her support. Then, Leah revealed the truth—on the TTC of all places. | As told to Juliann Garisto | May 16
No. 3 “I saw my friend’s boyfriend on Tinder. We decided to ambush him”
When Isabella, a 29-year-old freelancer, found out her friend’s beau was still on the apps, she started a group chat with the rest of the girls. Then she spent weeks laying the groundwork for their revenge. | As told to Juliann Garisto | May 29
No. 2 “I got married to a guy I’d known for only a few months. Then he got cold feet”
Holly, a 34-year-old teacher, thought she’d discovered love at first sight. But, after a whirlwind marriage, her husband suggested they live apart. That’s when she got back on Hinge and picked up a boyfriend to add to the mix. | As told to Juliann Garisto | June 7
No. 1 “After my date, I had to get my tampon removed in the ER”
After a few pitchers of beer and Slippery Nipple shots, Elizabeth, a 23-year-old student, hooked up with her date in the bar bathroom—but she forgot she had a tampon in. Until the next morning, that is, when the situation became painfully clear. | As told to Juliann Garisto | May 23
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