My First Big Failure

The Flop Heard ’Round the Pasture

I’d like to tell you that my first big failure was something truly monumental, like accidentally setting the family ranch on fire or losing a horse during a group trail ride. But alas, my big fall happened in a much humbler but no less humiliating setting: high school prom. Specifically, in the gymnasium of Telluride High, beneath a budget disco ball and too many balloons, where I completely botched my first chance at teenage romance.

I was a ranch kid in boots that were just a little too scuffed and a cowboy hat I swore I wouldn’t take off, despite my date politely begging me to leave it at home. I was the shy kid with more experience wrangling cattle than expressing feelings—a lethal combination when faced with the emotional minefield that is high school. My date (let’s call her Clara—not her real name, because some failures don’t need to haunt you and a second party decades later) was the epitome of confidence in rhinestones. She sparkled, she laughed with her friends, and she danced like someone who genuinely wanted to be there.

I, however, spent most of the evening standing awkwardly by the punch bowl, trying to calculate the exact right moment to ask her to dance (spoiler alert: I never did). When she finally asked me whether I’d like to join her on the floor for a slow song, I panicked. Instead of saying “yes” like any sensible human being would, I nervously mumbled something about the punch being “unusually citrusy” and walked away. Not toward her—to the bleachers. THE BLEACHERS. Who does that?

What the Bleachers Taught Me

This wasn’t just about awkward teenage clumsiness, though it was definitely that. What I see now, looking back, was that this cringeworthy moment set the tone for one of the most important lessons I’d eventually learn: risking failure is required to move toward connection, love, and growth.

In that gym, amidst soggy crepe paper streamers, Clara wanted to give me a shot at connection. And my fear of messing it up was exactly what caused me to mess it up. It’s ironic, isn’t it? Relationships are built on trust and vulnerability—two things I was thoroughly unprepared to offer that night.

But failure doesn’t always stay in the moment it happened. Like a particularly clingy barn cat, it can follow you, leaving lessons in its wake if you’re willing to learn.

Here’s what I uncovered from my first big failure.

Stop Overanalyzing; Start Acting

I’ve had years to think about that moment by the punch bowl. And while it’s painful to dredge up memories of my adolescent social skills, I now know what went wrong that night. I was too focused on anticipating the perfect response, too afraid of saying the wrong thing, and too stuck in my own head.

Overanalyzing is a natural reaction when vulnerability is involved. You want to get it right. But here’s a harsh truth I learned the long (and embarrassing) way: the pursuit of perfect timing, perfect words, or a perfect version of yourself will only leave you stuck at the starting gate.

If I’d just said “yes” and joined her on the dance floor—even if it had been awkward, even if I had stepped on her toes—it still would have been a better memory than the one I made for myself.

Failure Isn’t the End, It’s the Fork

Here’s another thing prom taught me: failing isn’t the same as failing forever. At the time, I decided that my disaster with Clara meant I wasn’t cut out for dating. For a while, I avoided anything that looked like romantic vulnerability. Instead, I threw myself into other things: tending the ranch, getting better grades, and mastering historical anecdotes for our family’s trail rides. Basically, I played it safe, which was predictable yet boring—even for me.

It wasn’t until college that I finally learned to embrace failure for what it actually is: a fork in the road. Every failure leaves you with a choice. Do you let it stop you, or do you let it shape a new direction? Clara may have had the glitter, but failure gave me grit.

I started saying “yes” to things that scared me. Yes to coffee dates with people I wasn’t sure I had chemistry with. Yes to public speaking assignments (even though my first one felt like getting bucked off a horse). Yes to taking risks that wouldn’t guarantee success. And wouldn’t you know it? Those yeses eventually brought me here, to a place where failure doesn’t scare me as much as standing still does.

Practical Takeaways from a Recovering Wallflower

Now, I’m not going to preach about prom forever. Let’s distill some action from those awkward bleacher moments. Here are a few big lessons I’ve learned about relationships and life since my epic teenage stumble:

  • Take the Dance. Metaphorically or literally, say yes to the thing that scares you. Connection always starts with a first step.
  • Perfection Is Overrated. Authenticity beats flawless execution every time. Be awkward. Be nervous. But for goodness’ sake, show up.
  • Failure Never Wastes Itself. Every stumble teaches something, whether it’s about courage, timing, or the importance of not hogging the chip dip at a party.
  • Embrace “What’s Next?” Failure opens doors to better paths—ones with people or opportunities more aligned to who you’re becoming. Look ahead, not back.

Closing the Loop

Years later, I actually ran into Clara at a Telluride coffee shop. She had a toddler on her hip, a husband in the corner reading a dog-eared paperback, and a smile on her face as we exchanged pleasantries. (And yes, she still sparkled.)

Our brief conversation was warm and full of life updates—which reminded me of something important. My awkward prom failure wasn’t life-ending, nor did it define my future. In fact, failing with her freed me to have different adventures, ones that have shaped me into someone who says “yes” to the dance now—cowboy boots and all.

So, to anyone hesitating at the edge of their own metaphorical dance floor, here’s my advice: try anyway. It might be a flop. It might be awkward. But failure? It’s proof that you’re in the arena. And that, far more than perfection, is where good things happen.