There’s a moment in every well-laid plan where things start to unravel. For me, it was halfway through a hike—an overly ambitious, ill-conceived hike—on a first date. This was supposed to be my chance to impress Lucas (not his real name) with my outdoorsy, adventurous self. Spoiler: it did not go as planned. At all.

Lucas and I had met at a mutual friend’s backyard barbecue. He was the guy who laughed at all my jokes just a little too enthusiastically, and I didn’t mind one bit. When he asked me out a few days later, I suggested something bold and different. Why settle for coffee or a glass of wine when we could climb a literal mountain together?

Lesson #1: Overestimating yourself is not a personality trait.

“It’ll Be Fun!” (A Famous Last Lie)

The trail I chose wasn’t just any trail—it was The Chief in Squamish. For those unfamiliar, The Chief isn’t a leisurely forest stroll. It’s a steep, thigh-burning climb that taunts you with its three rugged peaks and Vancouver-worthy bragging rights at the summit. But why did I think it was a good idea for a first date? The reasons were as flawed as they were optimistic:

  1. It sends a message. I wanted to let Lucas know I’m a cool, Pacific Northwest-ish kind of woman. Outdoorsy, ruggedly independent, possibly owns a flannel crop top.
  2. Shared struggle equals instant bond. Struggling uphill together would somehow, in my rom-com fantasy, translate to emotional intimacy.
  3. I forgot I hate uphill anything. Enough said.

I should have known I’d made a rookie mistake when I picked Lucas up that morning, and he showed up clutching a single aluminum water bottle. No snacks. No hiking boots. Just some very white sneakers that had clearly never seen dirt before. I laughed nervously and stammered, “It’s not that hard,” as though convincing us both.

Twenty Minutes In: The Cringe Was Setting In

Here’s the thing about The Chief: it doesn’t ease you in. There are no scenic warm-up strolls, no chirping birds to distract from your climbing dread. Instead, there are stairs—endless stairs of uneven rock that seem like they were designed by someone actively rooting against romance. Lucas powered up the first stretch like the Energizer Bunny, while I wheezed behind, legs trembling in betrayal.

I tried to keep conversation light, but there’s only so much flirtiness you can muster when your lungs are staging a coup. At one point, Lucas turned around and asked, “Are you okay?” which, on a first date, officially translates to: “I’m kind of regretting all my life choices right now.”

To lighten the mood, I blurted out a joke about cardio being just another word for “trauma.” He didn’t laugh. Strike one.

The Turning Point (AKA: Rock Bottom on a Rock Face)

Somewhere around the halfway mark, the trail turned into bouldering territory. We’re talking ladders bolted to rock faces and chains you cling to for dear life as you scramble upward. I could see the expression on Lucas’s face—half terror, half “how is this my Saturday?”—as he realized there was no turning back.

That’s when I tried to play it off with humor (again, tragically). I misjudged how far away Lucas was and called out, “Welcome to your TED Talk: Surviving Type-2 Fun!” He didn’t respond. At that exact moment, I slipped on loose gravel and landed in a perfect cartoon wipeout: arms flailing, body sprawled, dust plume and all.

If there is any situation that evaporates sexual-chemistry faster than falling on your butt while yelling “fun,” I have yet to find it.

Post-Hike Reflections: What Even Was I Thinking?

We did make it to the summit, though not without increasingly awkward silences and a moment where I offered Lucas my trail mix like a peace offering. By the time we got back to the parking lot, it was clear we both wanted the day to quietly end.

Would there be a second date? No. Did I learn something? Oh, absolutely. Turns out, misadventure is the flame that forges great post-hike metaphors. Here’s what I picked up on the hike that was supposed to be cute, and ended up being a cautionary tale:

Avoiding First-Date Fiascos: What You Can Learn from My Mistake

  1. Start small. Skyline views and grand gestures look great on Instagram, but they’re terrible strategies for getting to know someone. First dates are about finding your footing, not proving you’ve scaled Everest. Think coffee and a walk down the Seawall before you commit to cardio disasters.

  2. Know your audience. If one person shows up with snacks and the other shows up with a single water bottle, you’ve miscalculated the vibe. Choose dates that align with both of your comfort levels—or, better yet, ask outright what they’d enjoy.

  3. Mutual connection > manufactured charm. I wanted Lucas to love the version of me that clings to chains on cliff faces like some ethereal hiking goddess. Instead, he got sweaty, self-deprecating me—revelation: that’s okay, too. Be the version of yourself that doesn’t try too hard.

  4. End things gracefully, no matter what. When we got back to the parking lot, Lucas said, “Well, at least we both survived.” Bless him. I honestly think he meant it. If you’ve had a rough date, let it go on a good note, even if good is wildly relative.

Why Misadventures Are (Weirdly) Worth It

When all was said and done, the hike didn’t dismantle my dating confidence forever. On the contrary, it became a hilarious talking point—one I’ve pulled out at multiple other dates since (thankfully, ones that did not involve bouldering). And while Lucas and I never saw each other again, he’ll always be the guy who taught me there’s no better cure for dating cringe than time and self-awareness.

Because here’s the thing: bad dates don’t define your worth. They’re just pit stops on the scenic route to finding someone who sees you, sweat and all, and thinks, “Yeah, I’ll stick around for this journey.”

Even if that journey doesn’t start with a mountain.