It started with a typo. Actually, scratch that—it wasn’t just any typo; it was the typo that launched a thousand texts, ignited the most awkward first date of my life, and ultimately brought me face-to-face with something I’d spent years avoiding. But I’m getting ahead of myself. Let’s rewind.

First Impressions: The Good, The Bad... The Sweater

Two years ago, I was newly single and equal parts terrified and intrigued by online dating. You’d think as someone raised by parents who once picketed a Nestlé plant over water rights, I’d inherited a natural boldness. Not so. My first foray into creating a dating profile felt less like putting myself out there and more like being the lone goose in an aerial hunt. Vulnerability + the internet = a recipe for panic.

Still, I cobbled something together:

  • Favorite pastime? Chasing sunsets and bad puns.
  • Dream vacation? National parks road trip—bonus points if there’s a campfire involved.
  • Greatest fear? Running out of coffee on a Monday morning.

It wasn’t Hemingway, but it was me. The pièce de résistance, however, was my main profile photo: a casual (but curated) picture of me hiking a Rocky Mountain trail sporting a mustard-yellow sweater. Let’s pretend it wasn’t the same sweater my mom called “criminally unflattering” every Thanksgiving. Suffice to say, I was trying.

Enter Emily. Her profile boasted everything I could want in a match: a love for the outdoors, a master’s degree in renewable energy, and—this was key—a deep appreciation for below-average dad jokes. We matched, and I fired off a clever opener. Or at least I thought it was clever until autocorrect betrayed me.

Instead of saying, “I can’t believe we haven’t crossed paths hiking Chautauqua yet,” I accidentally sent: “I can’t believe we haven’t crossed pants hiking Chautauqua yet.”

Yes. Crossed pants. My thumbs sabotaged me—weaponized hilarity against my will.

Laughing at the Cringe

Emily, thank every trail-bound deity, thought it was the funniest thing since that one rebel chip in the Pringles can always getting stuck on its way out. She replied, “Crossed pants—bold first move. If we play our cards right, there’s always bungee jumping.” At this point, my cheeks were redder than a Flatirons sunrise, but I rolled with it. We texted non-stop for a week.

Our first date was an evening hike—classic Boulder vibes. This is where I learned that while I can help write policy on sustainable land use, I apparently cannot walk and talk near rattlesnake habitat without tripping over my own two feet (and nearly Emily’s in the process). You know those rom-com meet-cutes where someone spills coffee, and the other person thinks it’s adorable? This wasn’t that. In fact, if there were an award for Most Graceful Person Falling Uphill, I wouldn’t even have received an honorable mention.

And yet, as I brushed dirt off my perpetually unflattering mustard sweater, she encouraged me to laugh. “If you can survive this without wanting to ghost me immediately, we might just be onto something,” I joked. “Survive? This is the most fun I’ve had on a date in years,” she replied.

Spoiler: She meant it.

The Moment That Changed Everything

We made it to the summit, where the sun was spilling over the Rockies like melted orange sorbet. As we sat catching our breath, she turned to me and asked a question that knocked me sideways: “When was the last time you let yourself just… be bad at something?”

My brain stalled. I thought about my work, my writing, even my Spotify playlists—all curated, all polished. Then I thought about how long it had taken me to craft my dating profile just right, only to have it derailed by one rogue autocorrect. “I honestly don’t know,” I admitted.

Emily smiled and said, “Well, congratulations. You’re currently succeeding at failing. Enjoy it—it’s freeing.”

That moment stuck. It wasn’t just about dating anymore. I realized I’d spent so much time trying to control every impression I made, I’d forgotten how to embrace imperfection—the kind that makes you relatable, or genuinely interesting. Emily and I dated for a while, but she gave me something bigger than relationship potential: the freedom to let go of perfect.

Your Dating Profile, Unfiltered

Thanks to that cross-pants moment, I’ve come away with wisdom I wish I’d had years ago. Crafting an online dating profile isn’t about projecting polished perfection. It’s about leveling with people—showing enough of your quirks that someone can spot the best parts of you. Here’s how to do just that:

1. Toss Perfection in the Backpack

If you’ve rewritten your “About Me” section more times than Martin Scorsese has picked up a director’s chair, pause. The best parts of you aren’t in the overthink. Write like you’re explaining yourself to a friend at a coffee shop. Are you into obscure board games or memorizing bird calls? Say so. Odds are, someone out there finds that delightful.

2. Skip the Résumé Listing

Your dating profile isn’t LinkedIn. Instead of “avid hiker,” try, “Most likely to race you to the summit for the last granola bar.” Show, don’t tell.

3. Embrace the Typos (Within Reason)

I’m not saying you should intentionally sabotage yourself and autocorrect “fun-loving” to “fungus-loving” (unless that’s your thing), but don’t get hung up on perfection. Sometimes a typo can be a built-in ice-breaker.

4. Let Humor Do Heavy Lifting

Humor is like trail mix for your dating profile: essential and endlessly versatile. Not sure what to write? Share the weirdest playlist you’ve curated (“Songs to Listen to While Waiting for my Burrito Bowl” is a personal fave). Or admit something embarrassing—preferably not my snake-stumble.

5. Prioritize Authentic Over Exotic

Your love for skiing fjords might get you extra swipes, but if you’d rather Netflix binge and eat double-stuffed Oreos on Fridays, own that. The goal isn’t to hook the most matches; it’s to hook the right ones.

Closing Thoughts: Faceplant Your Way Forward

Two years after that mistyped first message, I still think about Emily’s advice. Letting go of the need to be flawless has changed the way I date, the way I write, and honestly, the way I live. That typo I dreaded turned into laughter, which turned into the kind of connection I didn’t know I needed.

So, from someone who managed to embarrass himself in both text and person—and still came out the other side—here’s the deal: The best things in dating happen when we’re a little messy and human. Let your quirks roam free, embrace the cringe, and, above all, give people a reason to want to “cross pants” with you.

And hey, maybe they’ll even love your mustard sweater too.