Let’s say you’re the Regional Managing Cupid for the greater Toronto area and you’re working on your “The state of dating in the city” presentation for the big annual Valentine’s Day conference.
You might start with some stats. Like the fact that Toronto’s pool of singles is growing: the number of single, never married people rose by 47,310 or 5.9 per cent between 2016 and 2021, and the number of divorced people rose by 2,535 or 1.7 per cent.
Or that “gym,” “dogs,” “kindness” and “humour” were the most popular keywords on Toronto’s Bumble app profiles in the past two months. And that the top three date activities listed on Canadian Tinder profiles are “hiking,” “concert” and “drinking.”
But what word sums up what it feels like to look for love right now in Toronto? “Dismal” came up multiple times when we spoke to local singles, first from 36-year-old engineer Michelle Kim.
“I think it’s becoming really challenging to connect with people,” said Kim, who finds dating apps “exhausting” and “so forced.” She feels nostalgic for the pre-digital dating days of yore. “Working in an office downtown, you could run into the same people in the elevators or at the coffee shop near work, casually make the eyes at each other, and start chatting,” she said. “These days, with working from home, the internet, social media, dating apps, we’re all connected but isolated.”
Alexandra Newbould, a 45-year-old courtroom sketch artist, also described dating now as “dismal,” pointing to the lack of social skills in Toronto. “Men here are not used to banter. Foreigners are a different story, but men from here tend to look at you like you’re crazy if you speak to them, say, sitting at a bar,” said Newbould, who has previously lived in Panama. “Even if I make a benign comment about the weather or, ‘Wow, no coat hangers, eh?’ I can sense this, ‘Oh no, I’m married, I have to talk out of the side of my mouth so she doesn’t keep going,’ or, ‘Hm, is she crazy?’ Or they just don’t know how to react.”
Newbould feels that dating is “so much worse” now than in the past, especially on the apps. “People are jaded, they ghost, or there are so many people on there that it’s like rooting through an entire town with all its rubbish, trying to go by a few pics and a dumb question, then having to chat, then meet and maybe it’s a no still,” she said. “It’s too time consuming.”
It’s possible that dating isn’t actually more dismal than it used to be, but we’re talking about it more — such as on “Are we dating the same guy?” Facebook groups. “With social media and the way women can communicate with each other en masse, we’re waking up to the fact that dating disappointment is more normal than we once thought,” said 32-year-old Chloe Bow, who was in a long-term relationship for most of her twenties before calling off her engagement. She’s a relationship counsellor turned founder of Toronto Girl Social, which hosts events to help women make friends. “In the past, there was a tendency for women to believe that something was wrong with them when they were unsuccessful with dating, but with more of us sharing our stories online, we’re seeing a pattern in the behaviours of men and realizing, ‘It’s not us — it’s them.’”
On the other side of this heterosexual gender divide? Edward, a 36-year-old office clerk who asked to go by his first name, described the atmosphere as “Cold War paranoia,” and referenced a line from the sci-fi horror film “The Thing”: “Nobody trusts anybody now, and we’re all very tired.”
Edward feels there is a “heaviness” to our world now that makes dating difficult. “Everyone is paranoid about each other, but especially women. Women don’t know who to trust. They are hyperaware that men hide who they really are,” he said, adding that he feels this is largely justified. “They don’t know what subreddits he reads, what podcasts he listens to. Men are quickly learning when to shut up about certain topics. There is a script for ‘the liberal guy’ and it’s so easy to say the right words.”
It’s also easy to say the wrong ones. “I used to love talking about gender studies stuff on dates — I got an A+ in Feminist Literary Theory at York — but with the Justin Baldoni and Neil Gaiman controversies, a man calling himself a feminist is a huge red flag now,” he said.
Edward was in a decade-long common law relationship that ended last year. He isn’t on dating apps but uses Instagram like one; in the last year, he had three “successful hookups or relationships” with women who slid into his DMs.
He’s noticed some major differences in the dating scene. Being sober is more mainstream: “I think it’s a red flag for a man to drink on a first date now.” Boundaries and expectations are much clearer: “It’s such a relief knowing you don’t approach strange women in public. If that pretty lady wants to talk to me, she’ll make the move.” And consent is a more normalized part of the dating ritual: “For the first kiss, it’s not weird to ask, ‘Can I kiss you?’ or ‘Do you want to kiss?’ anymore. In fact, I feel like many women prefer it these days.”
In the minus column: Dating is far more expensive than it was a decade ago. And he feels a pressure to constantly self-optimize. “I’m always trying to get to a stage where I’ll be ‘ready to date’ or I’ll be good enough to be an attractive boyfriend. It’s like Zeno’s Paradox, where I’ll never catch up to the tortoise,” he said. “I’m not well-read enough, rich enough, fit enough to be a viable candidate on the dating market.”
For Chris Poletek, a 28-year-old who works in software sales, moving to Toronto from Mono, Ont., a few years ago came with a dating culture shock. “This city is so different from growing up in a small town, and seeing those traditional relationships where people meet in high school or college and settle down and have a family,” he said. “The phrase that describes it best is ‘commitment issues.’ People here struggle to commit to people.”
A big piece of this, he thinks, is the “illusion of options” here. “It’s so transient, and there are so many people,” he said. “People feel like they have so many options at their fingertips that if somebody is not 100 per cent the perfect fit, they run to the next person.”
Poletek creates videos on TikTok, and the last date he went on via an app was a glimpse into a uniquely modern phenomenon: Dating while somewhat internet famous. “The person had seen my social media stuff before and was very well-versed in my life, and was very prompt to bring it up on the date,” he said. “It was a weird situation where you’re meeting someone who knows a lot about you.”
Or, at least, the incomplete, curated version. “People sometimes have preconceived notions of you before they meet you, based off of what they see online,” Poletek said. “I’ve had it said to me, more times than I can count on my fingers and toes, ‘Oh, you’re not what I thought you’d be.’”
Like many daters, he struggles with the app double bind: They aren’t pleasant to use, but it can feel like there’s no other way to meet people. “If I sit at a coffee shop with a book, is someone actually going to come up to me? Probably not. If I go out to the bar, is somebody going to come up to me? Maybe, but are their intentions to actually date me or do they just want to take me home tonight?”
While these frustrations are common to many big cities, Poletek has encountered one uniquely Toronto phenomenon: “The Miami Effect,” where locals find themselves compared to the lavish dating rituals found a 3.5-hour flight south. “Girls will get flown out to Miami, and they’ll stay in these accommodations, they go out to the clubs, they go out to the yachts, and everything is paid for,” he said. “And then they’ll come back to Toronto and say, ‘All the men are trash here because they don’t do the things that Miami men do.’”
As a result, Polatek said, he’s encountered women who look down on what an average 20-something Toronto man can offer them. “Some of the girls I know will go on their own girls’ trips, and they’ll be out to dinner and a random guy will just pick up the tab for them. Then they’re like, why doesn’t this happen in Toronto?” he said. “The level of wealth and what people do for work here is entirely different, and you can’t compare apples to oranges.”
Dating coach Shannon Laliberté spends a lot of time asking Torontonians why they think they haven’t found what they’re looking for. “Usually they blame external sources — the people they go out with, the apps, the dating pool — and they very rarely actually take a look at their responsibilities in their relationships,” she said.
A common stumbling block is differing expectations. “I hear from a lot of people: ‘We went out, and then the communication dropped off. I messaged them and it took until the end of the day to reply.’ Their expectation is that they’ll be responded to quickly, because they expect the person to be as excited as they are. That could be true, but it could be that they’re just busy.”
Her average client is in their late thirties, but Laliberté has worked with people on both ends of the age spectrum. “People in their twenties will often say what they want, but they’ll have really high criteria, and whether they’re aware of it or not, a lot of fears of getting into a relationship,” she said. “They find lots of excuses or reasons to prevent themselves from having what they want.” A recent Gen Z client said she’d met someone she really liked but dumped him after finding out he was in a dangerous occupation, calling it “too high risk.”
Among older daters, Laliberté has noticed that many people in their fifties and up are much more open to pursuing romance out of the once-rigid box of marriage. “For some people, another lifelong commitment isn’t what they’re looking for, but they don’t want to be totally alone,” she said. “Maybe we don’t cohabitate but we live close to each other, or maybe I don’t have a boyfriend or girlfriend but I have people I go out with and they’re great company but we don’t have any expectations of each other. People light up when they realize they could have that.”
Asked for one way to improve the dating experience in Toronto, most daters we spoke to cited more places to meet people in person. Enter Andrea Lo, host of more than 80 Toronto Dating Hub singles’ events attended by around 3,000 singles in 2024 — including “Jet Ski speed dating.” In the past four years, she says at least two marriages and many six-month-plus relationships have resulted from these events.
In Lo’s opinion, Toronto offers incredible opportunity for those looking to date. Go anywhere else, she said, and you will likely realize how much more restrictive those dating pools are. “Whether you’re a single mom or dad, with or without kids, there are people like you out there. Whether you do or don’t want kids, there are people like you out there. If you’re poly or LGBTQ, there are all of these options,” she said. “On top of that, Toronto is very multicultural. If you’re Jewish or Hindi or Catholic, whatever your background, you have choices.”
That’s true now more than ever. Lo said that post-pandemic, “a lot more people have jumped into the dating pool” out of loneliness. “You’ve got people looking for threesomes, you’ve got people who are travelling and passing through.” But that can lead to overwhelm. “There’s all this noise. If you’re looking for a long-term relationship versus something casual, it’s hard because there are so many people on their own different journey.”
Of course, all these options can be a double-edged sword. But if dating is a numbers game, you can’t ask for better odds than in a city of three million hearts.
