I was 27 years old the first time I traveled on an escalator alone.

Now, before you close this tab and judge me as a man entirely unqualified to face modern life, let me explain. My fear wasn’t irrational… okay, maybe a little irrational, but it wasn’t baseless. When I was five, I tripped getting onto an escalator at a downtown Toronto department store during the tail-end of a Boxing Day sale. My shoelace got sucked in—yes, like one of those cautionary tales designed to scare kids. A mall employee had to shut the whole thing down while I screamed bloody murder. To this day, you can tell my parents are still just a little emotionally scarred by the memory.

That formative moment turned escalators into metal monsters in my mind: grinding, clinking conveyor belts eager to devour sneakers, raise public humiliation to a fine art, and expose my inherent clumsiness. Stairs, I reasoned, were simpler and safer, even if my calves occasionally hated me for it.

By adulthood, logic clearly wasn’t driving the bus—I mean, people move houses on escalators in Ikea. But fear doesn’t really care about logic, does it? It hides in the corners of your life, disguised as practicality or quirkiness. My quirk just happened to be a staircase-purist ideology. That’s harmless enough, right? At least until you’re late for a meeting because you avoided the one escalator shortcut in the subway station.

It took dating—and a very specific, slightly humiliating first date—to face this fear. Let me tell you the story.

The Date That Changed It All

Picture this: a rainy Tuesday evening in October, downtown Toronto. A friend had set me up with this incredible woman named Emma (not her real name, but let’s roll with it). Emma: witty, whip-smart, and laugh-out-loud funny. We decided on dinner and a charming indie bookstore nearby for browsing afterward—the kind of casual-but-impressive first date ensemble every Torontonian secretly hopes to nail.

Things were going great. We were bantering like we actually belonged in one of those manic-pixie 2010s rom-coms. Until, of course, we boarded the subway.

At Bloor-Yonge station, the moment I’d spent most of my adult life artfully avoiding crashed into me like a TTC rush-hour crowd: two stories of escalator stared me down, unrelenting in its polished chrome arrogance. "Good," Emma said, pointing at the moving staircase. "We can grab dinner faster if we take that one."

I froze but tried to mask my terror as casual disdain. "Oh, uh, I usually take the stairs."

She arched an eyebrow. "What? Why? It's so much slower."

"Well, uh, cardio is really important," I stammered. Emma gave me a look. You know the one: politely amused, vaguely skeptical, and 100% unimpressed—a trifecta that only a really confident person can nail on a first date.

I knew I had two options. Own up to my ridiculous escalator phobia, or triple down on cardio culture and hope she didn’t Google "why millennials are obsessed with stairs." Neither felt like a winner.

But something about Emma made me want to push through my embarrassment instead of dodging it. So I blurted it out, all at once: "Okay, listen—I’m afraid of escalators. Always have been. It’s a whole thing. It started when I was a kid. I get stuck at the top, overthink getting on or off, sometimes panic and back out. Am I oversharing yet?"

Instead of laughing or walking straight to a different date with a less-complicated stranger, Emma smiled. "That’s weirdly adorable. Okay, let’s take it together. I’ll hike the stairs with you later if it doesn’t work out."

She didn’t make me feel small, just… human. Which is exactly what I needed to face this micro-monster of mine.

Lessons from Escalator Therapy

There we were: me, gripping the left rail so hard my knuckles were the color of steamed rice; and Emma, standing beside me with the quiet patience of someone who calms bees for fun. With her encouragement and zero judgment, I made it to the top. And just like that, my fear shrank—maybe not into nothingness, but into something manageable.

Was it easy? Nope. But did I stumble less afterward? A hundred percent yes, figuratively speaking. Looking back, the experience wasn’t just about conquering a fear of escalators—it was about breaking through the walls we all put up around trivial things that feel enormous. Which made me wonder: What other bits of "harmless avoidance" could be holding me (and maybe you) back?

Here’s what I learned:

  • Acknowledge It: Be real with yourself about what you’re afraid of, even if it feels tiny or embarrassing. Naming it out loud—to your mind, a journal, or even a patient new date—diffuses so much of a fear’s scary power.

  • Change the Frame: My fear wasn’t really about escalators—it was about messing up publicly and looking ridiculous. When I started framing the situations as "chances to practice laughing at myself" instead of "moist pits of shame," my brain relaxed. Imagine putting that advice into a dating profile.

  • Take Small Wins: Conquering fear doesn’t have to be a grand event. That one short ride on the escalator? That was a win. Everything else builds from there. Baby steps are still steps.

From Fearful to Flourishing

That date wasn’t just a chance to get to know someone else—it became an unexpected lesson about knowing myself, too. Fears dig their roots deep, but so does confidence, and overtime those small wins started adding up. By our third date (yes, a third—we’re all rooting for me here, right?), I was voluntarily taking escalators on my way to meet Emma.

And trust me: if a lifelong escalator-phobe like me can face the moving staircase of doom, you can tackle whatever weird, wacky, wonderful fears you’ve been avoiding. It could be giving a heartfelt toast at your best friend’s wedding. Or stepping onto a gym treadmill that somehow always feels like the physical embodiment of judgment. Or finally being honest with someone about your feelings when you’ve spent years perfecting the "play it cool" persona.

Every little fear we overcome builds toward progress. And, sometimes, that progress starts with letting yourself trust someone enough to take the first shaky step—literally or metaphorically.

Oh, by the way, Emma and I didn’t make it past a few dates (turns out, our love languages didn’t exactly mesh). But for what it’s worth, I’ll always be grateful I met her, just for that rainy evening when she turned a terrifying subway escalator into a stage for victory.

Your fear might look different than mine. That’s okay—it’s yours to face in your own time. But when you’re ready, I’ll be cheering from the top step.