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

The Fear of Getting It Wrong

Growing up in a family where traditions were as firmly rooted as the ancient oaks on our property, I developed a deep, gnawing fear of imperfection. The Winslow lineage doesn’t exactly reward trial and error; it rewards tradition, precision, and knowing which oyster fork to use at a clambake. Even flirting felt like a risky endeavor in my teenage years, lest I somehow break an unwritten maritime code.

To this day, my biggest fear—aside from accidentally addressing someone as “captain” who isn’t one—is the fear of failure. Or, more specifically, the fear of what happens when a relationship (or any deeply personal endeavor) doesn’t chart the course you pictured. What if I make the wrong decision? Choose the wrong moment to be vulnerable? Or get cuffed to the wrong someone for a lifetime because I missed some glaring red flag amid the heady aroma of sea-salted romance?

Here’s the ironic twist: I plunge into relationships anyway. Why? Because I’ve learned that avoiding connection is far scarier than the possibility of getting it wrong.

The Day My Lobster Boil Became a Boil-Over

Allow me to share a quick cautionary tale: Picture this—July 4th, Kennebunkport. Red, white, and blue bunting flapped proudly, and neighbors popped corks at a seaside lobster bake. I’d invited someone I’d been dating for a couple of months, a man who seemed charming until you looked too closely at the empty ballast of his conversational skills.

As the sun set and the crowd prepared for fireworks, I decided to “switch things up” and tell him something deeply personal—an impromptu confession about my anxiety around disappointing others. His response? He stood there, mallet in hand, mid-crack of a lobster claw and said, “Oh. Weird.”

Reader, it stung. Not just the comment, but the wasted vulnerability. I shrank a little that day, kicking myself for trying to deepen a connection that was clearly as shallow as the tidepools. But here’s the thing: that awkward moment wasn’t the end of the world. And it didn’t define me as a person or a partner. It was just a bad fit—a lesson wrapped in butter-slick fingers.

That moment clarified what I fear most: not rejection itself, but sitting out entirely, stifling my impulses because I’m afraid of the fallout if things don’t work out.

The Three-Step Plan to Outsmart Your Fear

Spoiler alert: fear doesn’t pack up and leave. It’s not an uninvited guest at your lobster bake; it’s a lifelong shipmate. But it doesn’t have to steer. Over the years, I’ve developed a few strategies for acknowledging the dread while also choosing to connect anyway.

  1. Ask Yourself, “What’s the Worst That Could Happen?”
    More often than not, the answer is embarrassment—an awkward pause, a misjudged joke, crying in front of someone during a heartfelt (or wine-fueled) confession. At its core, embarrassment can sting, but it also has an impressively short shelf life. No one is crafting a documentary about the time you accidentally quoted “The Notebook” verbatim on a first date. People understand mistakes. They make them too. Trust me on this.

  2. Treat Every Fear as a Teachable Moment.
    Remember that time I opened up to Mr. “Weird”? It taught me that vulnerability is my strength, not a liability—and that I don’t need applause when I share something real. These small, potentially cringy moments give us clarity. They weed out fair-weather partners while drawing us closer to the ones who truly want to know us.

  3. Dare to Laugh at Yourself.
    Self-deprecating humor is your most reliable life raft. Case in point: One summer, I tried to impress a date by navigating a small sailboat myself. Somewhere off Cape Porpoise, I managed to snag the jib on something (couldn’t tell you what!) and nearly capsized us. I was mortified, but my date just laughed—and then we laughed together. That moment of vulnerability turned out to be the most charming part of the entire day.

From Fear to Freedom

Here’s what I’ve learned, and it was as much a revelation for me as it might be for you: opening yourself up for connection is frightening. Whether it’s admitting you like someone more than you originally planned to or allowing someone to see your messy, unsorted internal life, there’s always risk. You might not get the reaction you’re hoping for. Someone might call your most personal truth “weird” (seriously, though… still mad about that one).

But the alternative is scarier—not trying at all. Sitting silently across the table because you’re too afraid to say what’s on your mind. Keeping every relationship on the surface to avoid the possibility of rejection. Eventually, you realize that avoiding the sea altogether just leaves you stuck on the shore.

On those days I feel gripped by fear, I like to think of storytelling traditions in maritime culture. Sailors didn’t share their best tales from times when waters were calm and danger-free. Their legends and lore came from the storms—the battles they fought and the lessons they learned when the wind turned.

And isn’t that what relationships—what life, really—are all about? Storms may blow through, but so does the chance to chart your own course (or find a capable first mate to weather it with you). My advice to you: Embrace the choppy waters. Eventually, your sea legs will grow steady.

So next time you’re tempted to hold back because fear is whispering in your ear, lean in and say: “Well, this might get weird.” You might make a mistake, but you’ll also make memories—and that, dear reader, is always worth the risk.