There’s a photo that haunts me. It’s from my first professional byline years ago, taken for the “About the Author” section of the now-forgotten article. I’m grinning awkwardly, giving off the same vibe as a bad LinkedIn profile pic—the kind where someone asks you to “look natural” but now you’ve forgotten how hands work. I hated that photo almost as much as I hated rewriting that particular article… over and over. At the time, I thought it was a one-off bout of writer’s block. Nope. It was just the start of what would become the most difficult piece I’ve ever had to write. Spoiler alert: that piece wasn’t about dating or romance (ironic, given where I work now). It was about the complexities of gentrification in Toronto. Romance feels simple in comparison.

But before I tell you how a deep dive into condo towers and cultural erasure changed me as a writer (and person), let’s back up. Like any good relationship story, we need the backstory.

Chapter One: Falling for the Dream

Toronto seduces you like a first crush with access to a record player. Anyone who lives here long enough knows the feeling—your heart beats a little faster when you walk through neighborhoods like Kensington Market or Queen West. Every graffitied alley and quaint bar patio whispers potential, as though this city is the cool older kid who’s letting you into their world.

Growing up in Riverdale, I’d already felt all of Toronto’s charm. Its blend of cultures, music scenes, and hole-in-the-wall eating spots shaped my worldview—and my taste in late-night snacks. It only made sense that I wanted to capture Toronto’s streets in my writing. I dreamed of being the kind of writer who tells rich, sweeping stories about overlooked communities while sipping expensive espresso in a rainy café window. In other words, I wanted to be just pretentious enough to be taken seriously.

And, oh, the topics I could tackle: housing inequalities, urban development, why all the cool coffee shops had somehow become yoga studios overnight. This was my "meet cute.” I thought my ideas and I were soulmates. It was thrilling…until I tried to write about them.

Chapter Two: The Honeymoon Ends

The editor pitched it to me: a deep, thoughtful exploration of how Toronto’s mom-and-pop shops—the ones that smelled like freshly baked breads or incense—were vanishing. Many were being replaced by luxury condos and chain stores so sterile you’d assume they were designed by an IKEA intern in a hurry. It wasn’t just a local story; it was a universal one. Gentrification is happening everywhere, from Brooklyn to Brixton, but this one hit home (literally).

What I thought would be a straightforward piece—gather quotes, weave stats into a narrative, hit “send” on the email—became an emotional labyrinth. The shop owners I interviewed told heartbreaking stories, like Caroline, whose bakery closed after 23 years because the rent had tripled. (Her blueberry crumble could’ve ended wars. I’m certain of it.) There was also Miguel, who ran a tiny record shop on the Danforth, forced to shutter when a three-story condo moved in next door and cut off his main foot traffic.

Each person I interviewed had one thing in common: they saw Toronto changing in ways that made them feel exiled from their own city, like falling out of love with someone who didn’t even notice. Writing these accounts wasn’t hard because the stories were dull—it was hard because they were too alive. How could I make space for their stories without them sounding like caricatures? How could I uphold their truth while also remaining unbiased?

Fun fact: I almost quit halfway through. I’d rewritten the opening paragraph about 14 times (yes, I counted). Nothing felt right. My editor suggested I hit pause and take a walk, so naturally, I walked around Kensington Market—the same neighborhood I’d been writing about. It was drizzling, and as I passed a café with only two customers inside, I realized something heartbreaking: this café used to be Miguel’s record shop.

Chapter Three: The Breakthrough

What I learned that rainy day is a piece of advice I still rely on today: write the hard things as though you’re writing a letter to someone you care about. I stopped trying to be the detached journalist and started writing the article as if I was talking to my close friends, the ones who’d also grown up in Toronto and witnessed the gritty, messy, beautiful evolution of our city.

The article finally came together, but not without more hair-pulling edits and a final round of “this still isn’t good enough” drama. In the end, the published piece wasn’t perfect (what is?), but it did the job. Caroline’s bakery stayed in my piece as a cornerstone, leading to a bigger profile done by another paper. Miguel ended up gaining enough attention to open a pop-up shop.

And me? I learned that sometimes, the hardest things to write can feel like pouring yourself onto the page. You’re raw, uncertain, and maybe a little tired, but the truth makes every syllable worth it.

Chapter Four: What It Taught Me About Relationships

You’re probably wondering what this has to do with dating or relationships. By this point, you’ve either decided this whole metaphor is working, or you’ve already scrolled off to TikTok. If you’ve made it this far, let’s connect the dots.

That experience taught me that relationships—whether romantic, platonic, professional, or even the one you have with your hometown—require honesty. It’s uncomfortable to confront the realities of change or try to put into words how someone (or somewhere) has hurt and inspired you in equal measure. But doing so is necessary to grow.

Here’s the kicker: the hardest things to write aren’t just about articulating your feelings; they also require accepting them. The same goes for love, where it’s easier to ghost someone than to admit things are fizzling out. Or to play it cool instead of telling someone you really, really like how they laugh at your bad jokes. Vulnerability takes courage, whether you’re telling your partner how you feel or telling a city what it’s becoming.

Final Thoughts: Never Stop Writing (or Loving)

Without giving into clichés about “follow your dreams” or “always speak your truth,” I’ll say this: the hardest piece I’ve ever written forced me to be kinder, both to myself and those I was writing about. If gentrification could teach me empathy, what else could my writing teach me if I stopped taking myself so seriously?

So, whether you’re navigating the ups and downs of a relationship or staring down a blank Word document that feels like it might eat you alive, take it from me: it’s okay to struggle. The hardest stuff often makes room for the most growth. And who knows? Maybe that growth will inspire your next chapter—blueberry crumble optional.