A first date in Toronto.
Dating in Toronto has an entire subculture dedicated to its tumultuous, treacherous and downright filthy nature, from Facebook groups for sharing bad dates to countless TikTok story times. The consensus is that the city's dating culture should be condemned, and yet we still keep coming back.
As a dating columnist and a certified single girl who cut her teeth and heart a few times in the Toronto dating scene, I'm happy to share that you can find the perfect person to split your rent with; you'll just have to go on a few dates first.
Trust me, I've seen a few success stories.
So before you spiral into a pessimistic black hole filled with a paralyzing fear of living in Toronto as a single-income household, here are the five dates you'll most likely have to go on before you find The One.
The marathon date
It started as coffee at 1 p.m. on Sunday, and next thing you know, you've spent five hours learning about someone's family traumas and their favourite colour.
The marathon date sneaks up on you.
It begins as a small, low-commitment get-together that should last an hour, only to spiral out into an all-day event.
Now, the marathon date can be good or bad.
Worst case scenario, you're a people pleaser at the whim of your date who keeps suggesting secondary and third locations across the city to which you helplessly agree to. Coffee at Jimmy's turns into lunch and a walk around town and two hours later, you're in Kensington Market licking an ice cream cone, wondering if you'll ever see your family again.
Best case scenario, you're having the time of your life, and drinks turn into dinner, which leads to dessert, then a cappuccino and maybe even a happy ending.
Now that's a marathon you won't mind running.
The world's most random venue
The first six months of dating is basically an agreeability challenge where you pretend to be easy-going, light-hearted and down for anything.
Toronto is filled with amazing date nights, from paint and wine classes to elegant dinners out, but not everyone has the same vision when it comes to the perfect Saturday night.
Inevitably, this will lead to your partner taking you to the most obscure location at least once in your dating career.
For me it was a convenience store on Queen West (I'd rather not get into it). For you, it could be Swiss Chalet, their family members' vow renewal, an EDM concert in the East End or even a night at Medieval Times.
The key identifier of this date is that the venue is somewhere you'd never go to in Toronto of your own accord, but in the pursuit of love, you make an exception.
During this date, you'll be a good sport, and the minute you get home, you'll FaceTime your BFF to recount and revel in all the cringe details.
Although you may surprise yourself and end up having a great time.
The walk and talk in Trinity Bellwoods
A walk in Trinity Bellwoods is the fast food drive-thru of dating.
Chances are this is a date you scored on a dating app where neither one of you is quite sure about the other, so a public meeting with a 15-minute shelf life is all you want to commit to.
You take your dog out for a walk in Trinity Bellwoods, so why not take your social life out for a stroll? It will most likely start with an overpriced coffee at the White Squirrel Coffee Shop and end in an awkward side hug.
You'll marvel at all the dogs, watch a group of 20-somethings attempt to cross a slack line and do circles around the park as you sip your coffees.
Will this be the worst date you've been on? No, but it will be the most forgettable.
The Bay Street Beauty date
Bay Street is Toronto's very own Wall Street, and just like New York, you'll find plenty of investment bankers and finance bros that take you to Earls, King Taps, Harbour 60 or Cactus Club Cafe for happy hour.
A Bay Street beauty will wine and dine you with expensive drinks and a nice meal, but chances are they're going to be checking their email at the dinner table and talking about their ex.
Now, not every Bay Street beauty will casually drop their salary into the conversation and try to take you home on the first date, but chances are if you're dating in Toronto, you'll unfortunately, run into at least one.
Bonus points if they happen to be wearing a puffy Patagonia vest over their dress shirt and make a big deal about picking up the bill.
The date that isn't a date
Ideally, a date is a pre-planned event with a reservation or at least a time and place set.
But as a single person in Toronto, you will end up being invited to countless last-minute "hangouts" at bars like Belfast Love, Paris Texas or any bar on King West that dances the fine line between date and casual get-together.
These dates will most likely happen at 9 p.m. or later and will lead you straight into the dreaded situationship territory.
If you don't know that is, it's when you're unofficially seeing someone but the relationship has yet to be defined even though you're consistently seeing each other.
So, while a late-night hang may be enticing when you're a few drinks in on Saturday night, you'll be left confused in the morning about what exactly transpired.
Was it a friendly hangout in a sexually charged setting or a romantic outing?
My advice is if you're looking for anything serious, you may want to avoid these ambiguous dates at the start of a budding relationship or just keep things casual.
Dating in Toronto isn't always as bad as it's made out to be, but to find your perfect peach, you may have to bite the bullet and go on a few rotten or semi-sweet dates.
I mean, with a population of over 6 million people, you'd think the city singles would find a way to make it work — if only for the sake of their golden doodles.
This article's right-hand cover image was used for illustrative purposes only.
