The Challenge I Didn’t Think I’d Survive

It started as most bad ideas do: overconfidence and a false sense of calm. “You’ve got this,” I’d told myself, pacing the wooden planks of the dock at sunrise. Birds swooped low over Lake Tahoe’s glassy surface, the water so still it felt like I was standing on an oil painting. It was the kind of morning that tricks you into believing you’re invincible. Which, spoiler alert: I’m not.

The challenge wasn’t a grueling mountain climb or a wilderness survival test. It was something far more terrifying—a first date with the human equivalent of an unsolved Rubik’s Cube. That’s right: my toughest moment wasn’t a daring backcountry adventure; it was trying to talk to someone I actually liked without combusting into a pile of nervous ash. Strap in, friends. This one’s a doozy.

Section 1: Frostbite or Flirting? The Paralysis of First Encounters

I’ll admit, nature has always been my safety blanket. Lost in a forest? No problem. Camping solo in a blackout winter storm? Piece of cake. But somehow, sitting down in a restaurant—for a dinner I intentionally planned—instead of hyperventilating into my napkin? It felt like trying to snowboard down the face of Mount Everest on a cafeteria tray.

They had everything. The kind of intimidating confidence that makes you wonder if they sleep on silk sheets or just…float above them. A laugh so dazzling it could’ve powered a small Tahoe cabin for a week. I felt completely out of my league, which is hilarious when you consider that I actually once climbed up Half Dome on a dare.

Before the appetizers even hit the table, I was doing mental gymnastics. “Should I start with self-deprecating humor? No, Trent, that makes you look insecure. What about asking thoughtful questions? Wait, no, that’ll seem interrogative. Is it too early for a joke about how bad I am at small talk? No, stay cool, Trent. BE COOL.”

Except, of course, I wasn’t cool. I was sweating like I’d just kayaked in July without sunscreen—and trust me when I say, lake sweat is very different from date sweat. They asked me about myself. I panicked and started talking about how birds in the Sierra Nevada hibernate in tree cavities, a fact NO ONE CARES ABOUT on a first date. Rookie mistake.

Section 2: The Awkward Middle Ground (AKA "Trial by Small Talk Fire")

Here’s what they don’t tell you about first dates: the appetizer portion can feel like an Olympic sprint where both participants are pretending they aren’t out of breath. Did I rehearse questions beforehand? Yup. But were they relatable to a normal person? Nope. I went straight for:

“What do you think about the emotional intelligence of Douglas firs?”
“No, no, wait, how about geothermal springs—do you have a favorite?”

Pro tip: This is not what people mean when they say “authentic self.” You need to ease into the quirks, not dump them on the table like you’re crowing your final Jeopardy! question. What’s wild is that somewhere between me explaining how mountain lions sneak up on their prey (as though this was useful party trivia?) and them giggling uncontrollably over the fact that I described redwoods as “tall introverts,” something shifted.

Their posture relaxed. I stopped sweating at a waterpark level. And we actually started talking—not just the scripted version of ourselves, but the real deal. You know, sharing dumb regrets (me: accidentally burnt sourdough starter during the 2020 bread craze), hopes (them: releasing an EP next year), fears (both: accidentally ghosting people we like because texting back requires NASA-level motivation).

Humor does something magical in these moments, especially when you have no idea where the conversation should go. It’s like the emotional duct tape of human interaction: not elegant, but incredibly effective. For example, when they asked me if I’d ever fantasized about leaving the mountains for the city, I said, deadpan: "Why would I trade bear encounters for crowded Trader Joe's encounters?"

Section 3: Lessons from the Fire

Am I going to pretend the rest of the date was smooth sailing? Absolutely not. I spilled water into their lap while trying to gesture “gracefully” mid-story (their hot take: “Wow, free ice bath”). I butchered the pronunciation of their favorite French wine (“Uh, the Fick-Sheenay 2016?” Reader, it was not pronounced like that). And I may have mistakenly thought “platonic” was a pasta dish for half a second.

But what I learned—and this is something the great outdoors teaches you too—is that challenges teach you resilience. Whether you’re wrestling with a too-heavy backpack on a snow-clogged trail or wrestling with the urge to obsessively apologize during a date, the key is to keep going. Let the awkward moments land. Own them. Laugh at them, when you can.

Someone once told me that hiking isn’t about reaching the summit; it’s about enjoying the grind of the ascent. That applies doubly to dating. The grind—the weirdness, the unscripted conversations, the parts where you’re wiping spilled soup off your phone screen because your aim was terrible—those are the moments where connection grows. Real connection doesn’t care about perfect. It thrives in the muddy, unfiltered places.

Section 4: Wilderness Survival and Emotional Survival (Basically the Same Thing)

So here’s what I can offer, from one perpetually-awkward human to another:

  • Learn to laugh at yourself. Seriously—I once motioned with a breadstick so aggressively that it snapped in two mid-sentence. We burst into uncontrollable laughter. Their exact words? “Well, that’s memorable.”

  • Stop rehearsing. Planning every second of the conversation is like pre-packing for a backpacking trip without checking the weather: you’ll either overprepare, underprepare, or prepare for a scenario that never comes. Let the conversation flow as unpredictably as a river, because that’s where the good stuff happens.

  • Be curious. And no, not weird-curious, like “Tell me the last seven books you read” by the main course. Instead, ask questions that spark joy for both of you. Think less “job interview” and more “campfire storytelling.”

  • Lean into awkwardness. The hiccups don’t mean the date’s doomed. Fumbling is relatable—sometimes charmingly so. I’ll opt for someone authentic over someone “perfect” any day. (Also, perfection is suspicious. Who wants that pressure?)

The Finish Line

In case you’re wondering, did I survive that first date? Did this challenge teach me what any marathon in the Sierras has: that hard moments temper the soul and grow the heart? Yeah. Eventually. We dated for six months before life took us in different directions. But what always stuck with me was their text afterward: “I don’t think I’ve ever laughed so much on a first date.”

And that’s worth more than a flawless French wine pronunciation any day.