How would you describe dating in Toronto? A disaster? Messy? Hell? Those aren’t our words; that’s just what a few residents have to say about their journeys in trying to find the love of their lives in the city.
Let’s face it, dating in Toronto is a wild ride. Sometimes it’s fun and flirty, sometimes it’s frustrating and complicated, and more often than not, it’s a little bit of everything. That’s why Now Toronto is launching This is Dating Now; a bold new series diving headfirst into what it really means to date in the city in 2025!
Forget the polished fairytales and swiped-right success stories. This is Dating Now is about the truth – the good, the bad, and the unapologetically ugly. We’re talking awkward first dates, ghosting sagas, surprising connections, open relationships, culture clashes, emotional growth, and everything in between. Each installment will feature real voices from across Toronto’s diverse communities, sharing their raw, unfiltered experiences in the dating world.
Take Toronto resident Maria N. for example, who was stunned to see the stark difference and as she says, “complicated,” dating experience here than when she lived in Vancouver, B.C. She recalled one of her worst dating stories that happened at a vegan restaurant. Note that neither Maria or her date, who also chose the restaurant, was vegan – red flag alert, perhaps?
“We ordered food for the table and he ate the entire thing!,” Maria explained.
“I was hungry. I didn’t eat. I was working for 10 hours and I was starving… And I was like, ‘Can I have some?’ And he was like, ‘Oh, sure.’ He left me the crumbs!”
It’s safe to say, there was no second date after that. In fact, Maria blocked him on all socials later that night.
Toronto resident MJ shared her bittersweet dating experience in the city too. After many years of hardships, she’s now in a thriving relationship. But it definitely wasn’t an easy road. She says one of her worst stories happened on the first date with a guy which seemed to be going smoothly… that was until he started playing his own music.
“I support everybody. I just didn’t think it was… I just didn’t think it was very good,” she laughed.
“But boyfriend now, he’s amazing! We just went on a date and then we have been inseparable ever since!”
Colin P. attributes the woes of dating in Toronto to the fact that the big city is frankly too small.
“If you’re dating around, you are most likely to bump into people that you may have dated before, have seen around, or whatever the case is, and ultimately that could lead to some awkward conversations,” he said.
Colin says his worst dating story was when he tried to be a gentleman and allowed a girl to drive his car, and immediately regretted it afterwards. The experience, which he described as “terrifying,” hasn’t changed how he feels about dating, however. In fact, Colin says it’s actually really fun to go on dates in Toronto.
“There’s so much to do. You know, grab some food and visit some of the sites and stuff here,” he said.
Whether you’re single, cuffed, situationshipped, or just here for the tea, This is Dating Now will shine a light on how love looks in a city that’s constantly changing. Think: interviews, hot takes, expert advice, first-date recommendations, and maybe even a few dating diary confessions.
Dating in Toronto isn’t just about finding someone, it’s about navigating who we are, what we want, and how we connect in this big city. And we’re telling the stories no one else is.
Make sure to check out This is Dating Now weekly on nowtoronto.com and on our social platforms.
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