"Here’s the thing about growing up in Toronto: it’s a city that constantly demands you find yourself while getting lost in everyone else. From the time I was old enough to take the 506 streetcar by myself, I was soaking up the energy of a city that felt like a relationship—complicated, colorful, frustrating, and endlessly rewarding. Toronto is a city that gave me my sense of self, my cravings for connection, and, oddly, my benchmark for love. This is the place that made me, for better or worse, and taught me what it means to truly know—and accept—someone (or somewhere) in all their weird, messy glory.

Building Relationships with Street Corners and Skylines

I know, I know—cities aren’t people. But Toronto comes awfully close. Growing up in Riverdale, I didn’t just learn to ride my bike; I learned to navigate unspoken neighborhood politics. Who gets the coveted backyard space at Rooster Coffee on a Saturday morning? Is it weird or cool that your parents know the guy at the Danforth cheese shop by name? These micro-lessons in urban etiquette weren’t just about living here—they were about connecting here.

Think of a long-term relationship: you notice all the quirks, the joys, the inevitable potholes. Toronto has been that for me. It’s always changing, upgrading like someone in a mid-life crisis who suddenly needs a $1,200 varsity jacket that used to sell for $40 in Kensington Market. But despite its shifting personality, it’s full of intimate familiarity—the way you’d spot a partner’s smile in a crowded room. That feeling of watching the sun set off the CN Tower’s glass edge is still the same, and it’s as comforting as coming home to someone who knows just how you like your tea."

But maybe the city’s biggest lesson is balance. Toronto’s vibe forces you to exist on a spectrum: flashy but grounded, ambitious yet practical. You think you’re dating Bay Street, but you’re really settling down with College Street. It’s taught me to appreciate dating (and navigating relationships) with nuance, a little grace, and plenty of patience. Something about sitting on an old patio chair on Queen West during a first date—it’s equal parts charm and chaos, which is honestly how most of us court in this city anyway.

The Love Affair(s) That Shaped Me

If Toronto is my main character, Kensington Market is the beloved (and possibly underappreciated) sidekick. As a teenager, the Market was my portal into identity—the vintage shops, the food stalls that taught me to embrace everything from empanadas to banh mi, and the people who looked like they’d stepped straight out of my parents’ best ‘70s stories.

One summer, I went on exactly five casual dates with a girl I met at the House of Vintage. She told me I had an ‘aura of someone who listens to too much Leonard Cohen’ (she was right, by the way). It didn’t work out for practical reasons—our schedules clashed, and it turned out the only thing we shared was a love of Film Noir Mondays. But that’s the other thing Toronto taught me—to be okay with connections that don’t lead anywhere. Sometimes a vintage store romance is meant to be just that: a snapshot.

Then there’s the harborfront—Toronto’s slightly distant, corporate-feeling cousin. It’s not where love stories usually happen, but hear me out. Once, I ended up on a very accidental first date there: a girl I’d met through friends suggested a walk, and somehow, we detoured into a concert at the Tall Ships Festival. We laughed about the absurdity of paying $15 to hear soft rock echo off Lake Ontario, but it’s still one of my favorite memories. Simple, unplanned, and sincere—Toronto at its best.

Lessons in Loving Messy Things

If you’ve ever been to Toronto during February, you know the city is, frankly, not at its most charming. Slush-filled streets, grey skies, and a TTC that seems to have psychic meltdowns every five minutes. And yet, even in the depths of its seasonal misery, my Toronto taught me about loving messy things. Because relationships—the good ones, the real ones—aren’t shiny skyscrapers casting perfect reflections; they’re alleyways coated in graffiti and puddles that ruin your boots.

This messiness showed up, too, in my early twenties when I started dating someone who lived in the Annex. The relationship felt like St. George Station: functional, a bit grimy, secretly charming if you looked closely. We went through all the typical ups and downs, from fighting over which bakery had the better croissants to deciding if our shared disdain for food trucks could sustain us. Spoiler: it couldn’t. But that messy middle phase taught me what love means when it’s not dolled up in romance-movie clichés. Sometimes love (like Toronto in February) is trudging through the slush because you care enough to show up.

Finding Your Signal in the Noise

Today, Toronto remains my lifeline, even as I’ve spent time in Vancouver and London. It’s taught me the fine art of navigating noise while searching for what matters—the people, stories, and places that feel like home.

Relationships, whether with cities or humans, are all about perspective. Toronto, for example, isn’t just one thing: it’s Drake concerts and obscure book clubs in secret basement bars. It’s a place you can bond over the insanity of property prices and get teary-eyed about hearing Gord Downie’s voice on the radio. The takeaway? Stop looking for perfection. Instead, embrace the mosaic—of a place, a person, or even yourself.

Feeling the vulnerability of sitting across from someone exposing their quirks is a lot like falling for a city knowing it can be flawed yet lovable. Deciphering someone’s taste in bagels from their preferred Spadina shop might just feel as nerve-wracking as figuring out what makes them tick when they say, “It's complicated."

Closing Thoughts

Toronto may be the place that made me, but the real gift is what it taught me about connection—with others, with myself, and yes, even with wobbly six-dollar café chairs at local dives. If you let your surroundings teach you, cities can be relationship whisperers. They edge you toward what matters most about love: patience, curiosity, and the willingness to weather the slush. So here’s to Toronto, for being my mirror, my mess, and my reminder that love (or a city) doesn’t always have to be perfect. It just has to be honest.