“I once helped lead a 25-mile horseback trek during a hailstorm. Another time, I stood on a moonlit ridge in the Rockies and improvised a spooky mining-town ghost story for a group of campers whose snacks were more sophisticated than their tolerance for altitude. And yet, none of those feats—aided by sturdy boots and a hefty dose of bravado—compares to the hardest thing I’ve ever done: writing an article about falling out of love.

Spoiler alert: it wasn’t pretty.

Love Is Easy. Writing About It? Not So Much.

For one thing, writing about relationships is like describing snow to an alien. Sure, I can tell you it’s white, cold, and best handled in layers, but your snow and my snow are going to feel as different as January in Telluride versus January in Tampa. Relationships are unpredictable and deeply personal, a chaos that doesn’t break down easily into tidy sentences. And try capturing heartbreak? That’s like lassoing a thundercloud.

I didn’t set out intending to dredge up my own messy history. But crafting the piece required revisiting old ghosts, those past moments when love turned slippery—moments when I’d stood on uncertain ground, lost for words, not unlike a tourist staring blankly at a foot-long horse stirrup.

The Article That Almost Did Me In

The assignment came during one of those rare patches in life when nothing particularly good or bad was happening—a real Tuesday-of-the-soul stretch. I was instructed: “Write about breakups, care about it, and make it universal. No pressure.”

This seemed straightforward enough. I mean, who doesn’t resonate with a good breakup story? From Olivia Rodrigo’s entire discography to the collective angst of mid-'90s rom-coms, breakups are practically a cultural rite of passage. But the further I dug into the topic, the more I realized how much real life complicates the happily-ever-after simplicity we've been sold.

Breakups aren’t neat. Sometimes, they’re not even definitive. They're more like old Western ghost towns—landscapes littered with artifacts of what was once alive, buzzing, and full of purpose.

And here’s where I ran into trouble. How could I write about heartbreak without offering a spoonful of my own heartbreak in return? Could I mold this article into something meaningful without digging through the emotional dirt of relationships that had bucked me off harder than any rogue trail horse?

Spoiler alert: No.

Revisiting the Ranch

I started the way I always do—with a yellow legal pad, a pen, and two cups of coffee so strong they practically hold eye contact. I flinched at sacrificing crumbs of my personal life to the page but remembered something my dad used to joke about whenever we’d have a rough day wrangling tourist groups: “Nobody climbs off a horse gracefully when their boots are full of mud.”

Translation? If you’ve got a messy story to tell, you might as well tell it with some honesty and grit.

That’s where the memories started rolling in:

  • The woman I bonded with over cowboy poetry and campfire chili, only for our relationship to unravel faster than my dad’s old lariat rope.
  • The time “it’s not you, it’s me” actually turned out to be true (and it hurt even more knowing that it wasn’t personal).
  • The occasions where timing failed us both, like two discounted frozen meals that missed the microwave boat by five minutes.

I began to notice patterns within these tales of romantic misfire. There were moments of growth but also red flags I’d brushed off like gnats on a trail ride. There was plenty I’d gotten wrong—timing, tone, expectations—but there was also a strange beauty in how even the heartbreaks had shaped the way I loved over time.

Lessons From The Trail

Somewhere along the way, the article transformed into something less like a polished breakup guide and more like an honest navigation tool for anyone who’s ever stared into the cavernous unknown of a post-breakup world. What I realized is this: relationships, much like life on the trail, depend on your willingness to adapt, stay curious, and sometimes let the terrain teach you.

For instance:

  • Know When to Dismount: Not every relationship is a thoroughbred built to run the distance. Sometimes it’s okay—even necessary—to climb off, dust yourself off, and walk it out solo for a while.
  • Read the Signs Early: Just like you wouldn’t ride nose-first into a lightning storm, ignoring red flags in a relationship is rarely a good idea. Trust your instincts and spare yourself the unnecessary thunderclap later.
  • Laugh at Your Mistakes: There’s nothing quite like standing ankle-deep in mud with a runaway horse to teach you humility. Relationships will humble you in the same way. Go ahead and laugh! You might as well while you’re down there.
  • Give Yourself a Scenic Route: After a breakup, give yourself the gift of time, space, and a long metaphorical trail to wander down. You’ll find clarity when you’re ready—not a moment sooner.

What I Took Away

In finishing the piece, I closed with a scene from one of my favorite trails in the San Juans. I described the way mountain storms roll in so fast you could blink and suddenly be in a downpour. It’s brutal, sure, but also breathtaking. Relationships—breakups included—are a lot like those storms. Painful, illuminating, and often followed by some of the clearest light you’ve ever known.

When I finally handed the article over to my editor, the relief I felt wasn’t just academic. Somewhere during the process of writing, I’d become grateful for every little storm I’d ridden through. It wasn’t perfect, but it was real—and that’s all that mattered.

So, was the piece worth the angst, the mess, and the hundred false starts? Absolutely. The hardest things in life—and that includes heartbreak—are usually the most worth writing about.

Take it from a guy who’s wrangled wild horses and even wilder emotions: no storm lasts forever, and the view when the clouds part? It’s nothing short of spectacular.