The Time I Lassoed Love—and Landed in a Thornbush

The Setup: A Big Idea (and Even Bigger Expectations)

They say fortune favors the bold. Personally, I think fortune just likes watching us make fools of ourselves—like some cosmic blooper reel. Case in point: my spectacularly doomed effort to impress someone while horseback riding one glorious summer evening. Horses and romance—what could possibly go wrong? Spoiler alert: everything.

The plan, at least in my mind, was foolproof. I’d invited Rachel, a friend-of-a-friend visiting Jackson for the summer, to join me on a sunset ride through the foothills of the Tetons. A pristine landscape, the smell of sagebrush in the air, two horses—it was a setup straight out of a Hallmark movie. My goal: to take this from casual acquaintance to “let’s see where this goes.”

Rachel seemed game when I suggested it, her eyes lighting up in a way that made me think I was onto something. But here’s the thing about big romantic gestures: they’re great… until they start unraveling faster than an old barn rope with a frayed end.

The Lead-Up: All Systems Go(ing South)

The evening started strong—or, at least, uneventful. I saddled up two trusty (ish) ranch horses, Rusty and Clover, whose resumes read: “experienced but occasionally rebellious.” Rachel was a little nervous around Rusty, but I assured her he was “basically a big dog in a cowboy hat.” (Lies. All lies.)

The golden hour hit, bathing the mountains in a soft, almost ethereal light. Rachel complimented the view, and I, emboldened by her enthusiasm, decided this was my moment to shine. I wanted to show her I wasn’t just some guy who wrote about nature; I lived it. So, naturally, I decided to demonstrate my roping skills.

Now, I’m decent with a lasso, a skill drilled into me by summers helping wrangle cattle. But to impress Rachel, I’d need to kick it up a notch—even if that meant roping on horseback, something best left to actual cowboys or rodeo professionals.

This, my friends, is where everything started to unravel.

The Disaster: How (Not) to Win Someone’s Heart

As Rachel marveled at the scenery, I spotted a downed tree—a nice, stationary target that wouldn’t fight back. Perfect, I thought. Turning to her with the swagger of someone who thinks they’re about to nail it, I said, “Bet you didn’t know I could be a cowboy and a writer, huh?”

Cue the lasso. I twirled it over my head—a little extra flare for the audience of one—and aimed for the log. Unfortunately, Rusty, sensing mischief, took that moment to channel his inner Thoroughbred. One second we were trotting along; the next, I was clutching the saddle horn like my life depended on it as he bolted forward. My lasso, in the chaos, found a new target: a scrubby juniper.

But wait, it gets better.

Rusty’s abrupt gallop spooked Clover, who, apparently taking her cues from Rusty, decided she wanted no part of this circus. Rachel, to her credit, hung on like a champ—until Clover veered off the trail.

Actually, you should know something about these trails: they’re not your average forest paths. These are Wyoming trails, filled with rocks, loose dirt, and, for a little extra spice, the occasional cactus patch. So while Rusty dragged me in one direction—toward the juniper I’d accidentally roped—Clover (and Rachel) charged toward a section of trail affectionately referred to as “The Gulch.”

By some miracle, both horses eventually stopped. My pride, however, didn’t survive the journey. Rachel managed to dismount with relative grace, while I extricated myself from a thornbush. My hat? Gone. My dignity? Also gone. And yet, Rachel couldn’t stop laughing—big, genuine belly laughs that made her whole face light up.

“You okay, cowboy?” she teased, brushing dirt off her jeans.

I muttered something about broken reins and rebellious horses, though, really, I knew: I was the problem.

The Lesson: When You Try Too Hard, You Miss the Point

Here’s the thing about trying to impress someone: it’s like over-salting a dish. A little effort goes a long way, but too much completely ruins the balance. My attempt to “wow” Rachel had backfired harder than a rusted-out pickup on a snowy morning, and it was all my fault.

What I’ve learned since then (and trust me, there’s been plenty of time for reflection) is that you don’t need grand gestures to connect with someone. Authenticity will always trump theatrics. Rachel didn’t care about my lasso skills—or lack thereof—but she seemed to enjoy my sheepish apology at the end of the evening. The shared laughter and mutual understanding of “well, that didn’t work” ended up doing more for our connection than the world’s best sunset ride ever could.

Whether you’re on horseback or navigating early dating, here’s what I’ll leave you with:

  • Skip the showmanship. It’s tempting to go big, especially early on, but genuine over flashy wins every time.
  • Know your limits. If you’re not a rodeo phenom—or, say, a Michelin-star chef—don’t pretend you are. Confidence is cool, but honesty is what builds foundations.
  • Embrace (and laugh at) the chaos. Sometimes, even your best-laid plans will disintegrate in a hail of dust and thornbushes. Roll with it. Nobody’s perfect, and most people respect someone who can laugh at their own blunders.

Rachel and I didn’t end up as a couple—turns out we were better trail-riding pals than romantic partners. And that’s okay. Now, when I share the thornbush story, it’s less about embarrassment and more about what I learned: When you stop worrying about impressing someone, that’s when you actually make an impression.

So go out there—metaphorical lasso in hand—and be yourself. Just maybe leave the literal rope tricks in the barn.