By the time I hit my late twenties, I thought I had the "risk-taking" thing down. I’d scaled scree fields in Rocky Mountain National Park during whiteouts. I’d quit a steady nonprofit job in Boulder to chase a poorly paid writing fellowship in Seattle. I’d even stood, feigning confidence, as a black bear ambled a little too close one summer on a backcountry hike. But the greatest leap of faith I’ve ever taken wasn’t about landscapes or paychecks—or bears. It was about love, or at least the wild pursuit of it, and it was terrifying in a completely different way.

The Email That Started It All

It began with an innocent email. My friend Sam—an incorrigible matchmaker and, frankly, someone with questionable taste in rom-coms—sent me a forwarded message with the subject line: “Your future wife???” Beneath it, there was a poorly taken group photo from a party Sam had attended in Chicago. Sam had circled someone (with the kind of squiggly red line detectives use to connect their suspects on a corkboard map) and added the caption: “Leah. Smart. Funny. Obsessed with Hozier. She’s tall. You’re tall. I see potential.”

Leah lived in Chicago. I lived in Boulder. And I was, for all intents and purposes, a homebody with little interest in dating across state lines. Still, something about her stuck with me. Maybe it was how Sam, who never sugarcoated anything, ended the email with, “Honestly, she’s way cooler than you. You should probably draft an apology for the disaster you’re about to make of flirting.” So, I took the leap—or maybe just tripped into it.

I wrote Leah a very awkward, deeply vulnerable email. There were typos. I misspelled “eclectic” but tried to cover it by calling it an ironic commentary on spellcheck. I signed off not with "sincerely" or "take care," but with, "Stay weird?" (I was immediately horrified.) Somehow, though, she wrote back—long paragraphs filled with wit, warmth, and a self-deprecating joke about leaning too heavily on Hozier lyrics during breakups. That was August. By October, I was buying a ticket to Chicago, feeling equal parts courageous and reckless.

Packing My Courage (And My Hiking Boots)

The flight to Chicago felt like preparing for some kind of battle. I could’ve written a survival guide for first long-distance meetups:

  • Snacks? Check. (Stress-eating trail mix was apparently my strategy.)
  • Overthinking flight delays or bad weather? On it.
  • Trying not to spiral into what if I’m catfished territory? A daily mental workout.

Sam, God bless him, didn’t help. He sent me a checklist of dating tips that felt more like advice for summiting Everest. “Be charming,” one line read bluntly. “Also, stop second-guessing your flannel choices. It is always flannel season.”

If there’s a word for the thrill-tinged anxiety of both wanting to meet someone and wanting to turn the plane around, I was living it. This felt like a true risk—not just because it was expensive (have you seen flights lately?) but because it required me to confront something scarier: the possibility of rejection, or worse, a painfully awkward encounter.

I was used to solo hikes, speaking my thoughts only at the occasional marmot. Real connection required letting go of that safe solitude. I felt unqualified. It wasn’t like I could pen-analyze my feelings into a perfect outcome. (Though if I’d brought my journal on that plane, you’d better believe I would’ve tried.)

Meeting Leah

Leah was waiting for me at Chicago’s O'Hare, wearing a yellow scarf that made her eyes look like two sunrises and boots that made her taller than my already-average 6’1”. She waved like a character in a rom-com—big, unselfconscious, like she’d spotted me at baggage claim years ago and had just been waiting for my slow-motion arrival.

And here was the kicker—she looked exactly like her pictures. No deceptive angles, no expertly curated Instagram filters. She was tall, authentic, and radiantly approachable. My brain immediately skipped to an ill-timed observation: Hozier’s “Take Me to Church” is probably not the right anthem for this moment, Miles.

The truth is, meeting someone for the first time has its own clumsy choreography. There’s the question of hugging or not hugging (we did, briefly, but only after a split second of mutually awkward hesitation). Then there’s the figuring out what to say after “Hi, how was your flight?” I stood there sweating slightly under my flannel, trying not to sound like I was interviewing her for a podcast.

We got through the worst of it in the cab ride to her apartment. By dinner, we’d found our rhythm, bantering about everything: how she hated “forest green” as a concept but loved the actual forest, how I thought pizza in Chicago was a verbose take on what nature intended pizza to be. It didn’t feel effortless—it felt earned, like two strangers learning each other’s tempo for the first time.

The Risks You Take for Love

Here’s the thing. Being willing to show up, to risk all the inevitable misfires and insecurities—that’s what makes dating artful. It’s like hiking a mountain you’ve never summited before. You follow the switchbacks, get waylaid by unexpected mud, and keep going anyway, hoping the view is worth it. (Spoiler: it usually is.)

Taking a chance on Leah was worth it—in ways far bigger than I had imagined. She wasn’t just kind; she was present in a way people rarely are anymore, the kind of person who asks a follow-up question when you mention your dream of writing short stories about Rocky Mountain marmots. Over the next few months, we flew back and forth between Boulder and Chicago, slowly building something that felt both exciting and grounding.

Was it easy? Absolutely not. Distance is a cruel editor, cutting down the best intentions into short, miscommunicated texts and staggered timelines. There were moments when it felt like it would be easier just to opt out—stick with hiking trails instead of flight paths. But working through those complexities showed me, for the first time, that deep connection often requires showing up in places you’re scared to fail.

Take the Leap (Yes, Even the Risky One)

So, what’s the payoff of greatest risks? For me, it wasn’t just about Leah—though clearly, she made the leap worthwhile. It was about tapping into something I’d avoided for years: vulnerability. Letting another person see the messy side of me (you know, that guy who overpacks snacks and overthinks scarf compliments).

What I’ve learned is there’s no guaranteed “perfect moment” to take a chance, whether it’s boarding a plane to meet someone new or daring to speak your feelings when you’re not sure they’ll be returned. (If you’re waiting for the universe to stage-manage your life like an indie film, you’ll miss the scenes worth filming.)

The risks that scare us the most usually hold the biggest opportunities for growth. They get us out of our ruts—the solo hikes and overly comfortable habits—and into life’s real adventure. I’m not saying every leap will be rewarded with cinematic payoff, but isn’t the possibility enough to try?

A Final Thought

Leah and I eventually parted ways—not because it didn’t work, but because sometimes life draws people together for moments instead of lifetimes. And that’s okay. The experience gave me more than a love story. It gave me courage and the reminder that the hardest—and most interesting—paths are the ones we don’t plan. Looking back, I wouldn’t trade the “risk” for anything, and I encourage you to leap, too. Because staying weird and taking chances? That’s where the magic happens.