"You’ll never make it.” Those were the words looping in my head as I tried to muster a grin for the dozen paddleboards beside me. We were on an “easy-breezy couples paddle” around Boulder Reservoir—so, of course, I was horrified to realize that I had absolutely no idea what I was doing.

The pressure was compounded by the fact that I was trying to impress someone. Someone I liked a lot. We were still in the new, sparkly stage where you don’t admit you hate kale smoothies or that you’ve only skimmed every book in your “To Be Read” pile. At that wobbly, watery juncture, I wasn’t just battling my lack of finesse. I was wrestling with the very real possibility that I might faceplant in front of this person and a flock of muscular, tanned strangers.

This should’ve been a date to treasure: the glow of the Colorado sun, endless sky, and a Pinterest-worthy afternoon-on-the-water vibe. Instead, it became a metaphorical mirror, holding up startling truths I didn’t know I’d need to confront. Turns out, that’s the thing about challenging moments—they hit you when you're least prepped, often wearing board shorts.

Let me break it down so, ideally, you can avoid looking uncool while clutching a paddle like it’s a medieval broadsword.

When Flirting Meets Flatwater: The Setup for Disaster

Let’s rewind. The paddleboarding invite came on the heels of an amazing third date. Serenading each other with obscure indie deep cuts? Check. Knowing glances exchanged over street tacos? Double check. This paddleboard thing? Honestly, it felt like the relational equivalent of “leveling up.” Adventuring together—even small-scale outdoor activities—can tighten bonds and set roots for shared memories. Or, in my case, test your physical and emotional equilibrium, in both senses of the word.

Here’s a fun fact I should probably have admitted: I’m not a big water guy. Growing up in Boulder, I’ve always been a mountains-and-forests sort of soul. Hiking? No problem. Camping? My jam. But open water? That split between you and the deep, alien unknown? That’s the realm where I feel most human—and not in the cute, relatable way. More the shaky, is-he-going-to-pass-out way. Combine that with my inner perfectionist’s refusal to admit fear, and you’ve got Friday afternoon's comedy of errors.

The Wobble Heard ’Round the Reservoir

We’d barely paddled ten feet when the tectonic plates of my self-confidence began to quake. My date, the picture of ease, paddled like they’d been doing this since birth. I, meanwhile, summoned the grace of a baby deer learning to walk.

It didn’t help that our mixed group included that one couple who just had to do everything tandem—complete with choreographed turns—and a fitness instructor named Lucas wearing a beanie in 85-degree heat. Lucas kept shouting things like, “It’s all about your CORE!” which my modest flannel-clad upbringing refused to respect. My core at that moment was strictly engaged in avoiding public humiliation.

I somehow lurched my way toward the center of the reservoir. This was a mistake. Wind rippled across the water, pushing my glorified rectangle of foam further from shore. I knew then that the next part of my journey would demand more than balance. It would demand…vulnerability.

Control is Overrated—and So Is Perfection

If I’ve learned one thing about relationships, it’s this: Sometimes the bond grows not when you’re polished, but when you allow others to see you completely unpolished. By the time wave #399 threatened to dunk me backward into the drink, I was ready to whip out an excuse, call it a day, and sulk into a burrito.

Instead, I laughed. I laughed at how weird I must’ve looked; I laughed at Lucas and his cryptic core-strength musings; I laughed at my date, grinning at my floppiness from their paddleboard, clearly trying not to yell, “You’re doing great” in a condescending tone. And in the process, I started letting go of that internal voice that kept screaming, "You’re blowing it. They’re going to think you’re a fraud."

By leaning into the absurdity, I accidentally salvaged the moment. I stopped prioritizing an ideal version of “how it’s supposed to look” and started enjoying “how it’s actually happening.” Wobbling into someone’s good graces, I realize now, has charm too.

Takeaways from the Paddleboard Panic

When I finally drifted back to shore, I was drenched but smiling. My date? Also smiling. Apparently, my flailing had come across as endearing rather than embarrassing. Who knew? The moral of the story—and yes, there has to be one—is that certain challenges don’t just test limits. They reveal them. Sometimes, that’s uncomfortably humbling. Other times, it clears space for real connection to take root. Here are a few lessons I paddled away with, mostly intact:

1. Honesty trumps flawless execution.
No one needs you to be a superhero all the time. It’s okay to say, “This isn’t my thing, but I’ll give it a shot.” Showcasing effort (even clunky effort) is often more attractive than showing off ease.

2. You don’t have to love every activity your partner loves.
Learning about your person’s interests is part of the process—but alignment doesn’t mean agreement. It just means being open and supportive. Maybe paddleboards won’t become “our thing,” but the stories from that day? They definitely are.

3. Master the recovery, not the stumble.
We all fall short sometimes—literally and figuratively. What matters is how you recover. By switching from self-critique to self-compassion, you can transform awkward moments into those you laugh at later.

4. Perspective is your best friend.
In the grand scheme of life, botching a date activity (or ten) isn’t the end of anything. In fact, it might be the beginning of the stuff that really matters: patience, understanding, grace under pressure.

5. Laughter wins hearts.
When in doubt? Laugh at yourself. People generally like folks who know how to lighten the mood, not folks who double-down on their ego. Bonus points if your self-deprecating humor is accompanied by an unintentional splashing sound.

Love (and Life) Is a Balancing Act. Literally.

Sitting here now, far from the reservoir’s edge, I can appreciate that the challenge wasn’t paddleboarding. It was surrendering control. Relationships aren’t about orchestrating perfection. They’re about participating—nerves, flubs, awkward moments, and all.

To be honest, I never did make it into the realm of paddleboard proficiency that day. But I left the water knowing I’d shared my most authentic self: goofy, vulnerable, and trying to paddle against the ridiculous current of insecurity. Was it smooth and graceful? Absolutely not. Did it count? More than I expected.

So if you’re staring down a scary or awkward moment with someone you care about, embrace it. Show up for them—and for yourself. Even when your metaphorical paddleboard feels wobbly, the real magic happens in the effort to stand tall anyway.

Turns out, even the roughest waters can teach us what it means to stay afloat.