If there’s one thing ranch life teaches you, it’s how to trust your gut—and also how not to pick a fight with a territorial moose in spring. But taking risks? That wasn’t exactly in my DNA. Sure, I could blaze through backcountry trails or scale a rock face without batting an eye, but putting my heart on the line? That was a whole different beast. Until one summer, I decided to do the unthinkable. I fell for someone entirely out of my universe and, instead of playing it safe, I leapt. Spoiler alert: It didn’t go as planned, but it shaped everything that came after.
Let me set the stage.
When Opposites Collide
I was 26, fresh out of my park ranger gig, with a sturdy pair of hiking boots and a less-than-sturdy dating resume. My social circles were as small as a Wyoming winter sunlit day—tight-knit and predictable. Then came Naomi, a medical resident from New York City who showed up in town for a weekend yoga retreat. She had a laugh that could topple the Tetons, and at the risk of sounding like an unnecessary subplot in a Nicholas Sparks novel, I was hooked. We met at a low-key barbecue one Saturday night. She spotted me tossing horseshoes and asked if I was “a real-life cowboy.” I told her I leaned more toward Wrangler than Marlboro Man—which apparently was charming enough to score me a date.
But here’s the thing: Naomi was effortless, polished, and urbane; I was rugged, a little awkward, and possibly wore too much flannel for her taste. She loved sake tastings and evenings at the opera. I once mistook kombucha for something you use to clean barn stalls. Still, opposites attract, right?
The Big Leap
Three weeks into casual hikes and moonlit talks, Naomi told me she'd be flying out to Denver for a conference. “It’s not too far,” I said, feeling uncharacteristically brave. “Maybe I’ll drive out and meet you there for dinner.” She smiled and said, “That could be fun.” Key detail: We didn’t finalize plans.
But that weekend, after 7 uninterrupted hours of white-line fever across the vast nothingness of southern Wyoming, I found myself in Denver with a hopeful heart and too much time to fill before our (kind of vague) dinner plans. Oh, and there was one more wrinkle: She wasn’t answering her phone. In hindsight, showing up unannounced without full-fledged confirmation was…bold. (Okay, let’s call it what it was—deranged optimism fueled by gas station coffee.)
The reality hit somewhere between looping the same block in downtown Denver for the third time and wondering if I should eat alone and call it. My worst-case scenario played out when her text lit up my screen: “So sorry—crazy day. Maybe we can catch up when I’m back in Jackson?”
I was crushed. For a guy more accustomed to worrying about bear tracks than love tracks, the humiliation stung. But I ordered a greasy diner burger, watched the bustling Denver streets from a window seat, and stewed in my rash decision. Somewhere between bites of too-salty fries and my second refill of soda, I asked myself: Why did you think this one leap would stick the landing?
The Fallout
It took me a while to reconcile what that trip really meant. On the surface, it was a flop. A wild, impulsive gesture that left me with nothing but sore legs and a dent in my dignity. But on a deeper level, it was also my wake-up call. Here’s the deal: It had less to do with feeling rejected by Naomi (she was gracious when I saw her back in Jackson, though our fling fizzled not long after) and more to do with realizing why I had taken the risk in the first place.
For years, I’d skated through my relationships on autopilot: no bold confessions, no grand gestures, no messy, vulnerable moments. It was safe, sure, but also deeply unsatisfying. Denver wasn’t about Naomi—it was about me shaking hands with discomfort and deciding that, just maybe, heartbreak wasn’t the monster I’d made it out to be.
Lessons From the Breakneck Denver Adventure
If you’ve ever found yourself leaning too heavily on the safety net in love, maybe my story can save you a tank of gas (and a mildly bruised ego). Here’s what I walked away with—besides a stern self-lecture on communication:
-
You Have to Risk Rejection to Find Real Connection.
For years, I’d avoided going all in, afraid that being vulnerable would hurt more than being alone. That Denver debacle showed me that even if your leap falls flat, the world keeps spinning. -
Put Yourself Out There—But Have an Actual Plan.
Want to be bold? Great. But maybe make sure the other person is on the same page before you show up in a new city. Love flourishes in spontaneity, but it still thrives on clarity. -
The Risk Is the Reward.
I didn’t get the romantic ending I envisioned, but that trip lit a fire under me. Being willing to fail spectacularly made every future attempt at connection seem less daunting. -
It’s Okay to Laugh About It Later.
At the time, I was mortified. But now? I tell that story at dinner parties to roaring laughter. Humiliation becomes hilarity, given time.
A Wild Heart Deserves a Wild Ride
I think back often to that shaky Sunday morning drive out of Denver. I was operating on three hours of sleep and a bruised ego, yet there was also something strangely uplifting about the open road back to Wyoming. I’d failed, sure, but I felt deeply alive. Heartache was no match for the mountains, and optimism had an uncanny way of re-sprouting, like wildflowers after a spring thaw.
If you’re sitting somewhere right now, wondering if you should call that person you’ve been thinking about, take that risk, or lean into the unfamiliar—you’ve got your answer. Do it. Even if it’s messy. Even if you end up standing alone in Denver, wondering if Google Maps lied about that sushi place being open.
Love is one part chemistry, one part timing, and eight parts guts. You can’t control the first two, but you can sharpen the third. Risk it. Leap. Whatever the outcome, you’ll have one heck of a story to tell later.
