Somewhere between the Annex and Leslieville, someone is asking ChatGPT how to reply to "Hey 😊."
Someone in King West is using AI to rewrite their Hinge profile before a Friday night out. Someone on the TTC is asking it for the perfect first message. Someone else, stuck on a delayed streetcar, is wondering whether "Hope you're having a lovely week" sounds too eager.
Welcome to dating in Toronto, 2026.
Toronto is Canada's largest city and, by extension, home to one of its largest dating pools — an estimated 2.79 million residents,1 with roughly 1.4 million of them single, according to the most recent national census breakdown of the city.2 That tracks with a broader national trend: the share of Canadians aged 15 and over who are single has climbed from about 33% in 1981 to roughly 45% today.3 Toronto, Montreal, and Vancouver consistently have the largest single populations in the country, simply by virtue of being the largest cities.4
Artificial intelligence has quietly become the newest wingman in a city known for being spread out, hard to socialize in after work, and, let's be honest, a little polite to a fault. It can help write profiles, suggest conversation starters, decode confusing texts, and coach people through the particular discomfort of small talk with a stranger on a patio in Yorkville. Nationally, 54% of daters now report using AI tools somewhere in their dating life, a 333% jump from the year before.5 Roughly 41% say they'd lean on AI for in-person conversation starters, and 40% want help crafting the "perfect" profile.6
None of this is necessarily a bad thing. Used well, AI can help people become more confident communicators. But it does raise one rather interesting question in a city where everyone's already commuting in from somewhere else.
Who exactly are you getting to know?
When Your Personality Has a Co-Author Most of us have edited a message before hitting send. That's perfectly normal. But there's a difference between taking a moment to gather your thoughts and having an algorithm do the talking for you — something that's become common enough that roughly six in ten dating app users now believe they've encountered an AI-written conversation at some point.7
Dating has always been about discovering another person's quirks, humour, and personality. If every message is polished to perfection by an algorithm, those wonderfully imperfect moments can start to disappear.
After all, nobody falls for someone because they used the ideal adjective.
People fall for someone because they laughed at the wrong moment on a packed King streetcar, made an unexpected joke about the weather changing four times in one day, or admitted they still haven't made it up the CN Tower despite living here for a decade.
Those moments can't really be generated. They simply happen.
Chemistry Doesn't Live in a Chat Window Technology has made meeting people easier than ever, yet Toronto singles report feeling more exhausted by dating than ever before. Nationally, 78% of dating app users report some level of burnout — emotional, mental, or physical exhaustion from the process — with the figure climbing to 79% among Millennials and Gen Z.8
It's not hard to see why people are pulling back. The average match rate for men on Tinder sits around 0.6%, or roughly one match per 167 right swipes.9 Bumble fares a little better at close to 3%.9 Add in a city where the person you matched with lives forty minutes away by transit and the date stalls out before anyone exchanges a number — over 70% of dating app conversations reportedly never make it that far9 — and it's easy to see why so many Torontonians are looking for something more direct.
That's one reason in-person dating events continue to draw people who simply want to meet someone without weeks of digital small talk and a TTC transfer standing between the match and the actual meeting. You learn more about a person in six minutes across a table in the Distillery District or Queen West than you often do after six weeks of carefully edited messages.
Body language. Eye contact. Shared laughter. Comfortable silences.
Those things don't translate particularly well through a keyboard — or an AI-generated opener.
AI Can Help You Start a Conversation What it can't do is create chemistry.
It can't recreate the feeling of making someone laugh unexpectedly over a drink on a Ossington patio. It can't capture the slight nerves before sitting down across from someone new, or the spark that comes from discovering you both have strong opinions about the Leafs.
Real attraction isn't built from perfectly crafted messages. More often than not, it's built from moments nobody planned — and definitely not moments a chatbot drafted for you on the subway platform at Bloor-Yonge.
That's why some of the best dates begin with conversations that are slightly awkward before becoming completely effortless.
The Best of Both Worlds We're certainly not anti-AI. In fact, it can be remarkably useful for Toronto's busy, spread-out singles. Ask it to proofread your profile, suggest a date idea beyond "coffee," or help you write a message you've been overthinking for three days.
Just don't let it replace the very thing someone here is hoping to meet.
You.
Because confidence is attractive.
Kindness is attractive.
Humour is attractive.
And authenticity will always beat artificial perfection — even in a city this spread out.
One Final Cheeky Thought If AI helps you get through the door, wonderful.
Just remember to leave your digital wingman on the platform when the date begins.
The rest is entirely up to you — and thankfully, no algorithm has figured out how to replicate that yet.
Looking to experience Toronto dating without prompts, rewrites, or AI-generated flirting?
MyCheekyDate has been bringing Toronto singles together in person since 2007 through relaxed, host-led speed dating events across the city. Because sometimes the best conversations are the ones nobody could have written.
Footnotes
Point2Homes, "Toronto, ON Demographics," citing Statistics Canada's 2024 population estimate. ↩
Mutual Match, "Is Being Single in Toronto Harder?" citing Statistics Canada's 2016 census — approximately 683,305 single men and 705,980 single women in Toronto. ↩
Psychology Today Canada, "How and Why There Are So Many Singles in Canada," citing Statistics Canada data — the share of single Canadians 15+ rose from about 33% in 1981 to roughly 45% by 2016. ↩
Global News, "Where are Canada's singles? The census found them" — Toronto, Montreal, and Vancouver have the largest single populations among Canadian cities. ↩
SwipeStats, "Best AI Dating Apps 2026" (May 2026), citing the Match/Kinsey Institute 2025 Singles in America survey — 54% of daters use AI tools, up 333% year over year. ↩
Psychology Today, "AI Use in Dating Jumps 333%," citing the 14th annual Singles in America study. ↩
Scientific American, "So You Fell for a Robot — 'Chatfishing' Is Taking Over the Dating Apps" (October 2025), citing a 2025 Norton study. ↩
Forbes Health / OnePoll survey of 1,000 U.S. dating app users, as reported by Global Dating Insights. ↩
CupidAI, "Dating App Statistics 2026," citing Business of Apps and public platform data (April 2026). ↩ ↩2 ↩3