My Greatest Risk

It all began with a butter dish.

I’d been eyeing it for weeks during my afternoon strolls past a certain antique store on Broughton Street. It was dainty—delicate blue flowers curling across porcelain, perched on an elegant scalloped tray. It wasn’t particularly practical (who even uses a butter dish these days?), but it spoke to me in the way old things sometimes do. On the day I finally went inside to claim it, I also walked out with something else: a tiny business card advertising that the shop owner’s nephew, Everett, offered sailing lessons for beginners.

Now, let me preface this by saying I am not the “adventure sports” type. I am the “polo shirt at book club” type. Or, at my riskiest, the “whispers Savannah ghost stories over wine on a Thursday night” type. The idea of boarding a sailboat—where things can tip, sink, or get complicated—was firmly in my “that’s for other people” column.

But I’d been feeling restless. Savannah, though richly adorned with charm and history, had grown too familiar. My predictable routine in its gaslit streets had begun to feel like that sweet but unchanging instrumental track my mother likes to play on repeat. I craved something new, something unexpected. So, bolstered by a moment of impulsivity (or temporary insanity), I dialed Everett’s number.

The Leap of Faith: Or, Why I Pretended to Like Rope Knots

When I met Everett at the dock, I immediately wondered if I’d erred. He was the walking epitome of a Patagonia catalog: weather-worn skin, wavy brown hair, and a faint whiff of cedarwood cologne. I, on the other hand, had shown up in oversized sunglasses, a vintage Lily Pulitzer sundress, and—regrettably—wedged espadrilles. I looked like I’d accidentally wandered into a J.Crew ad filmed on location.

“Have you been on a boat before?” Everett asked.

I paused. Did a ferry to Tybee Island count?

“Yes! Once or twice,” I lied with the confidence of someone who absolutely has not.

With that dubious starting point, Everett launched into a primer on sailing, covering topics like bowlines, tacking, and the importance of keeping an eye on wind direction. I nodded along, despite only catching every third word, because I was too busy watching him tie a perfect figure-eight knot in one fluid motion. I didn’t understand a thing, but I clapped enthusiastically. Who doesn’t perform better with encouragement?

Within the hour, we were on the water: Everett confidently at the tiller, I nervously gripping the side of the boat as if sheer force of will could keep me from falling overboard. Savannah’s golden hour cast warm blush tones across the river, and the sight was unspeakably beautiful. I found myself smiling, the kind that feels fresh and effortless, the kind you don’t question while it’s happening.

Of course, this was before Everett decided we needed to “ride the wind” and tipped the boat at a 45-degree angle.

Risk and Reward: The Sailor and the Scaredy-Cat

If there is anything more humbling than realizing you’ve been clinging to the wrong rope on a sailboat—while shouting, “I’m helping!”—I do not know it. I was sure I’d tumble into the water at any moment. My mind flashed through a thousand terrors: alligators, shipwrecks, ghostly recitations of Flannery O’Connor quotes while I dog-paddled to shore.

“Relax!” Everett shouted above the fluttering sails. “The boat leans—it’s supposed to!”

“Leans! You mean capsizes!” I hollered back.

Eventually, I noticed something: even though my pulse was racing and I wasn’t entirely sure what to do, I wasn’t, in fact, falling. The wind was strong, yes, but the boat—anchored by skilled hands and likely a small dose of sailor magic—held steady. We tilted into the invisible force like a couple bracing against a wild storm. It felt…exhilarating.

But the bigger leap of faith wasn’t the sailing itself. It was what came after.

Sailing Into (Uncharted) Romance

It turns out that spending two hours on a sailboat with someone changes the dynamic between “strangers” and “acquaintances” very quickly. Everett had clearly noticed my, let’s call it “beginner energy,” and admitted as much while we coiled the ropes back at the dock. “You’d never sailed before, had you?”

Caught, I thought about denying it, but instead I laughed. “Not even a little.”

Rather than teasing me, he smiled. “You did good.” And before I even knew what I was doing, I asked if he ever practiced sailing with passengers who were…less rope-oriented and more “good conversationalists.” My heart hammered in my chest as soon as the words came out.

“Maybe over dinner,” he replied, his voice easy but his grin teasing.

And that’s how I ended up drinking champagne with Everett under Savannah’s oaks the next evening, swapping stories about Lowcountry storms and the oddities of Savannah locals. Sailing might’ve been unfamiliar territory, but this—the swelling flutter of new romance—was something familiar and cherished. I could trust the rhythm of it.

What Sailing Taught Me About Taking Risks

Looking back, saying “yes” to that sailing lesson was the most significant risk I’d taken in quite a while, even if it seems small compared to, say, cliff diving or moving cross-country. Maybe because, after years of following a safe and steady routine, it was more than deciding to sail—it was the decision to shift the narrative I’d built around what kind of person I thought I was.

Here’s what I took away from the experience:

  • It’s okay to bluff a little—just not with your heart. So what if I exaggerated my nautical experience? What really mattered was my openness to the adventure. Taking risks doesn’t mean you have to lead with perfection. Fumbling is part of the fun.
  • Leaning in is scarier than it looks, but it’s worth it. Whether it’s the tilt of a sailboat or leaning into emotional vulnerability, the things that feel unstable often yield the greatest rewards. Trust yourself to find balance, even when it feels impossible.
  • You don’t have to risk it all to change your perspective. Taking a leap doesn’t mean you have to leap far. Start small: say yes to an invitation, suggest a date idea that feels “not your style,” or simply try something new—even if it’s just swapping your usual latte for cold brew (baby steps, right?).

The Butter Dish and the Bigger Picture

For the record, I did end up purchasing the butter dish. It sits on my kitchen counter now, a gentle reminder of the day I swapped familiar paths for the open water. It never gets used for butter—because let’s be honest, most of us are loyal to the tub of Kerrygold—but it’s there just the same, catching light and memories in equal measure.

Everett and I sailed together a few more times after that first outing, both on water and through the winding currents of early dating. Things didn’t last forever—I suspected it was because he loved the unpredictability of the open sea, and I loved the constancy of a bookshop corner—but the experiences we shared opened me up to adventures I never thought I’d seek. And that, I realized, was the whole point: to lean into a little adventure and see where the wind takes you.

Because in the end, whether it's tilting on a sailboat or falling for a dreamer in cedar cologne, the greatest risk isn’t tipping over. It’s standing still.