You know that sinking feeling when you realize your brilliant idea wasn’t so brilliant after all? Maybe it’s the moment your soufflé collapses despite what seemed like a foolproof YouTube tutorial. Or the second you hit “Reply All” on an email that was meant to stay private. For me, my most epic misadventure wasn’t in the kitchen or the office—it was in the wild, with someone I very much wanted to impress.
Allow me to set the scene.
The Great Outdoors and Even Greater Expectations
Her name was Erin. We met at a bookshop in Boulder (yes, people actually do that outside of rom-coms), and our first conversation was about Mary Oliver’s poetry. By the time she said, “Tell me, what is it you plan to do with your one wild and precious life?”—referencing Oliver's most famous line—I was already smitten.
After a couple of coffee dates, I decided to lean into my Colorado roots for our third outing. What better way to show someone you’re outdoorsy, capable, and adventurous than a day hike? I picked the perfect trail: something with enough elevation gain to be “impressive” but not so strenuous that it would leave us wheezing unattractively. The weather forecast was clear, the wildflowers were in bloom, and I’d packed a picnic she’d later describe as “charmingly rustic” in her Instagram post. (Okay, I hoped she’d describe it that way.)
But like many good plans, this one unraveled faster than I could tie my hiking boots.
When Confidence Meets Catastrophe
Our troubles began before we even hit the trailhead. In my enthusiasm to show I was prepared for anything, I packed the largest backpack known to humanity. I stuffed it with sunscreen, three different water bottles, a first-aid kit large enough to handle a zombie apocalypse, and our aforementioned "charmingly rustic" picnic. By the time I lifted it onto my back, I resembled a cartoon character about to topple over.
“You, uh, expecting to climb Everest?” Erin teased. I laughed along, masking the beads of sweat that had already formed.
Hiking with Erin felt great—for the first ten minutes. Then the combination of altitude, my overloaded pack, and a poorly-chosen breakfast of leftover pad Thai hit me like a brick wall. Erin, who was wearing a breezy, minimalistic fanny pack, bounced along as if gravity didn’t apply to her. Meanwhile, I felt like Frodo dragging the One Ring up Mount Doom, only Frodo didn’t have the added pressure of looking attractive while doing it.
And then things got worse.
A Trail of Trouble
Somewhere around mile two, Erin asked, “Hey, where are we, exactly?” It was an innocent question, but only then did it dawn on me that I hadn’t checked the updated trail map. Boulder’s trails are like spaghetti—beautiful but confusing if you’re not paying attention. Sure enough, we soon realized we had veered off the intended loop and were heading into uncharted (for us) territory.
At first, I waved it off. “Small detour,” I said, projecting confidence I absolutely didn’t feel. But when our “small detour” stretched into its second hour, Erin’s polite cheerfulness began to wane. The sentiment in her Mary Oliver quotes gave way to something that felt more “Survivor.” To top it off, storm clouds—completely absent from the morning’s forecast—began to gather.
There’s a very specific type of panic that sets in during moments like this. It’s a mix of embarrassment, fear, and the acute awareness that you are not, in fact, Bear Grylls. While I debated whether it would be more humiliating to admit we were lost or try to fake competence for a while longer, a sudden clap of thunder decided for me.
“We should head back,” Erin said, now firmly in charge.
Drenched, scraped, and trudging under a rapidly deflating ego, I made a promise to myself: if we made it out alive, I’d write an article about the ways a misadventure can teach you humility—and also how to win back some dignity when your date sees you at your worst.
So here we are.
What I Learned From Getting Everything Wrong
As much as I’d like to forget the soggy, mosquito-infested fiasco that was that hike, there are a few valuable lessons I carried away from it. And since I know I’m not the only person who’s tried and failed to impress someone they like, here’s my hard-won wisdom:
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Authenticity Trumps Impressiveness
Here’s the thing about trying to be impressive: it often reads as exactly that—trying. I wanted Erin to see me as rugged and resourceful, but I would have been better off being myself—a guy who loves the outdoors but probably doesn’t need to pack three kinds of granola bars for a five-mile hike. If you’re not into grand gestures or elaborate dates, don’t fake it. Even the Rockies can’t save a plan that doesn’t feel authentically you. -
Be Prepared, but Don’t Overcompensate
Yes, preparation is important, but so is knowing your limits and planning within them. Triple-check the map. Keep it simple. And for the love of all things holy, avoid the temptation to carry enough gear to outfit a small search-and-rescue team. Sometimes, less really is more. -
Laugh at Yourself (But Not Too Soon)
It’s hard to make light of a bad situation while you’re knee-deep in it, but hindsight works wonders. At that moment, Erin didn’t need me to make jokes about how ridiculous we looked sprinting down the trail in the rain; she needed me to take the situation seriously. Once we were safe in my car—muddy but unharmed—that’s when the laughter kicked in. -
Pay Attention to What Actually Matters
Looking back, Erin didn’t care whether the hike went perfectly. What she cared about—what most dates care about—is how we handled an imperfect situation. The fact that we survived the ordeal together, with no hard feelings, said more about our potential compatibility than a flawless day ever could.
How It All Turned Out
If you’re wondering, Erin and I didn’t end up together, but not because of that hike. We actually dated for a few more months before parting ways amicably. That day in the mountains taught me something that has stuck with me through every relationship since: people connect through shared experiences, not staged ones. It’s the messy, unplanned things that often end up mattering the most.
So the next time you find yourself stranded, soaked, or miles off course—whether on a literal trail or the path to someone’s heart—remember this: misadventures can be the best kind of stories. Just maybe pack a little lighter.
