What Scares Me the Most (and Why I Do It Anyway)

The Wave That Always Looks Too Big

Growing up in La Jolla, I was surrounded by people who were fearless—or at least seemed to be. My friends thought nothing of charging into the Pacific to surf waves that looked, to me, like moving skyscrapers. I, on the other hand, would stay waist-deep, watching them bob confidently over the swells while I nervously calculated my odds of survival should I wipe out.

The fear wasn’t the wave itself—it was the tumble. The idea of being held underwater, spinning with no control, gasping for air that might not be there. But inevitably, after standing on the shore for too long, my curiosity would nudge me toward the lineup. I could never completely ignore the little voice, equal parts scared and defiant, that whispered, “But what if you catch it?” That’s how I’ve approached most fears in life—not by eliminating them but by reckoning with them in a way that makes them feel worthwhile.

When I think about dating, I see the same pattern. If fear were an Olympic sport, romantic vulnerability would be my podium event. Yet, here I am—showing up, heart open, ready to paddle into the unknown.

Why Dating Feels Like Big Wave Surfing

Let’s start with some real talk: dating is terrifying. And I say this as someone who once accidentally picked up what I thought was a harmless sea cucumber only to discover it was a highly agitated octopus. (Ever see eight angry limbs flailing in protest? It’s a lot.) But unlike surprise marine life encounters, the terror in dating doesn’t come in a single, shocking moment—it’s slow, charged, and often indecisive.

Take the first date, for example. It carries the same energy as paddling up to a wave and trying to decide: Should I commit? Or is this going to crush me? It’s not just the wave—it’s the stories we tell ourselves about what’s going to happen if we wipe out. The brain whispers: “What if they think I’m boring? What if I spill wine on my shirt? What if they’re still secretly in love with Rebecca from accounting?”

But here’s something I’ve learned from braving both big waves and awkward first meetings: the stories our minds spin are almost always more dramatic than reality. Most of the time, you don’t wipe out. And if you do, it’s rarely as bad as you imagined. One time, on a date, I spent a solid five minutes raving about a “documentary” on Netflix about a surfing dog, only for my date to gently inform me it was an ad for dog food. Did I want to disappear into the Earth? Absolutely. But we ended the night laughing over fish tacos anyway, Rebecca from accounting be damned.

Brave Tiny Acts

So, how do you confront the fear without letting it paralyze you? Here’s what’s worked for me (in both surfing and dating):

  • Start small: Just like you wouldn’t paddle into a giant wave your first time out (unless you want an unflattering feature in a fail compilation), don’t pressure yourself to swipe right on someone who immediately intimidates you. Low-stakes chemistry is still chemistry—start there.

  • Find a rhythm: In the water, timing is everything, and that’s true for connections too. Not every person you meet will be your perfect match, so practice enjoying the process rather than expecting instant fireworks.

  • Let it be awkward: This one’s huge. You’ll fumble; they’ll fumble. First-date jitters, weirdly specific cocktail orders, sharing a snack only to realize they don’t eat carbs—it’s all part of the charm.

  • Ask better questions: Instead of falling back on the dreaded “So, what do you do?” try this: “What’s a skill you’ve never had but wish you did?” You’ll get bonus points for creativity, and it opens the door to a deeper, more memorable conversation. I’ve also found this to be an excellent cue to share embarrassing stories. (Example: My skill would be not-faceplanting while carrying a surfboard. Alas, still working on that one.)

The Fear Doesn’t Go Away—and That’s Okay

Here’s the kicker: fear doesn’t magically evaporate just because you face it once or twice. The next wave still looks big; the next date still feels full of potential cringe or rejection. But the difference is this: every time I’ve paddled out or shown up to meet someone, I’ve proven to myself that I can survive it. And that little reminder gives me the courage to try again.

In one of my more recent romantic endeavors, I found myself on a hike with someone I really liked but barely knew. Somewhere along the trail, they casually asked, “What scares you the most?” It caught me off-guard. At the time, I think I jokingly said, "Falling off cliffs," since we were walking next to a particularly steep drop-off—and because vulnerability in the moment felt scarier than any freefall.

In hindsight, I wish I’d said something truer. Like: “What scares me the most is putting myself out there and feeling like it’s not enough. But I do it anyway because that’s how I find the people and things that make my life richer.”

Lessons From Fear: What It Teaches Us About Love

If fear’s sole purpose was to stop us from trying, I’d probably still be standing on the beach, watching everyone else catch waves while my board collected dust. But the part of fear we don’t talk about enough is how it sharpens our focus. It forces us to choose what matters, because the very act of risking something means you’re investing in the possibility of something worthwhile.

That’s what love asks of us: to paddle out, even when the waves look high and our hearts feel unsteady. Because as scary as it is, there’s something irresistible about the what-ifs that live just beyond the shore.

You’re Braver Than You Think

So, did I ever conquer my anxiety about surfing bigger waves? Let’s put it this way—I’m not Kelly Slater (far from it), but I keep showing up. Some days, I catch something great; other days, I wipe out spectacularly. But each time I paddle back out, I remind myself: progress doesn’t come from playing it safe. It comes from taking the tumble, gasping for air, and daring to paddle out again anyway.

As for love, the same rule applies. No matter how nervous, self-conscious, or unprepared you feel, you’re braver than you give yourself credit for. So, what scares you most—and why might it be worth doing anyway? Go ahead, paddle out. The next wave you catch might just surprise you.