Some places seep so deeply into your bones that they shape not just the backdrop of your life, but the entire script. For me, that place is a worn, weather-painted house perched at the edge of Kennebunkport’s rocky shore, a short walk from where the tide has pulled in more lobster traps than I’ll ever attempt to count. It’s where generations of Winslows traded grand adventures for the humble rhythm of the waves, and where I learned the kind of lessons that make navigating relationships—romantic or otherwise—a lot like sailing in choppy waters. Spoiler alert: the ocean doesn’t care about your best-laid plans, and neither does love.
Home Is Where the Lobster Pot Boils
If you’ve ever stared at a tide chart trying to figure out when the boats will come in, you’ll understand there’s a rhythm to everything—waves, seasons, even people. There’s no rushing a receding tide, just like there’s no rushing your best friend through the agony of picking the perfect text to send after a great first date. Kennebunkport taught me patience. It taught me that some things—the good things—are on their own schedule.
Growing up in what locals call a sea captain’s home means the house has its own personality. The wood floors creak like they know secrets; the wind whistles through cracked windowpanes in a way that can only be described as opinionated. That house taught me to embrace quirks. If you can live with a home that insists on dripping salt air into every corner, you can handle dating someone with an unnecessarily strong opinion about pineapple pizza.
My family believed in balancing tradition with levity. Lobster bakes were standard fare, of course—complete with seaweed steamed over crackling beach fires. But alongside the clambakes were debates over the best jazz standards (Dad was adamant about Sinatra). Somewhere between schooner racing and debates over Cole Porter lyrics, I learned humor and curiosity as love languages. I became the kind of person who finds joy in asking her date if he had a “go-to sea shanty” growing up—because moments like that reveal more than any “What do you do for a living?” ever could.
The Tug of the Coastline
Sailing was a central part of life, and I’ll be honest: there’s no teacher quite like the Atlantic Ocean. Try trimming a sail while a nor’easter is barreling toward you—it’s like learning to communicate calmly while your partner is hangry. You will lose your cool once, maybe twice, but eventually, you figure out that teamwork beats a sinking ship every time. Sailing taught me to read the wind and adjust course when things don’t go as planned, which, surprise surprise, happens roughly 100 percent of the time in both relationships and ocean navigation.
Relationships, just like the weather off the Maine coast, can turn messy. But I’ll let you in on a secret—messy isn’t bad. Messy just requires direction. Sailors don’t throw down the anchor at the first sign of storm clouds. They double-check their heading, tighten the lines, and adapt. It's the same with love—if a little disagreement or unpredictability sends you sprinting back to shore, you’re in for a lot of lonely sunsets.
Lessons from Salt, Stories, and Style
Those rocky beaches and historic homes taught me the value of preservation: holding onto what matters while letting sea-swallowed sand slip through your fingers. My own relationships reflect this philosophy. Not everything (or everyone) is meant to be clung to; sometimes, the right choice is sitting by the shore, watching the tide take its course, and starting anew.
Equally important? Storytelling. Kennebunkport is a town built on maritime lore, where every front porch seems to hold a ghost story or an anecdote passed down from some storied schooner captain. It’s why I tend to look beyond the surface when someone tells me their “life story” on a date. Does it include twists, untold vulnerabilities, an unmistakable thread of humor? Ships all have a history. People should, too.
Finally, let’s talk style. There’s an unwritten rule in coastal Maine that you should project what I like to call “effortless preparedness.” A navy sweater, sturdy boots, and windswept hair that says both “I just strolled the shore” and “Is the regatta starting soon?” It’s subtle, but it tells a story—you’re not here for show, but you’ve got a carefully chosen anchor tattoo hidden somewhere. Kind of like how your online dating bio shouldn’t scream TMI or a rehearsed pitch but rather a snapshot: “Part-time sunset chaser, full-time taco aficionado. Will probably beat you at Scrabble, but don’t let that scare you.” Less is more, trust me.
Driftwood Lessons for Modern Love
Now, let’s get practical. What can a place like Kennebunkport teach someone about love, whether they’ve navigated a lobster boat or not? Here’s what I know to be true:
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Be Kind to Yourself, but Pack Snacks.
Lobstering rule number one: never go to sea without a sandwich or some emergency saltines. Dating? Same idea. Arrive prepared—not in an overachieving, write-a-sonnet-for-the-first-date kind of way, but don’t forget that little thing called self-care. Stay hydrated, bring gum, and for heaven’s sake, don’t skip lunch. Hangry flirtation is not the vibe. -
Everyone Has a Few Rogue Waves.
On the water, waves can come out of nowhere. Some are thrilling; others soak you head-to-toe. Life’s messy moments—awkward silences, poor timing, small misunderstandings—are unavoidable. Adventure happens when you don’t panic but ride those waves instead. Bonus: rogue waves are often the funniest stories later. -
Check the Weather, Know When to Anchor.
This one’s metaphorical. Take stock of where you are emotionally; is the “weather” good—clear skies with mutual interest—or is a storm of red flags brewing? Sailing through bad conditions just to avoid being alone rarely ends well. Drop anchor somewhere safe when you need to, and don’t feel bad about it. -
The Best Love Stories Age Like Weathered Wood.
There’s an understated beauty in finding something or someone durable—someone whose knocks and dents only make their story richer. When looking for connection, don’t get hung up on surface shine. Weathered wood has charm for a reason.
The Sea, the Shore, and You
Being shaped by a place like Kennebunkport means I approach relationships with both curiosity and reverence. The same way I admire the ghostly bow of an old schooner drifting in the harbor at dusk, I believe in preserving the quiet magic of people’s stories. If you’ve got a rocky beach like mine—a place, real or nostalgic, that anchors you—it’s worth returning to, if only in spirit. You’d be surprised how much clarity comes when you let the tide pull at your thoughts.
Because here’s the thing about the “place that makes you”: it never leaves you. It’s your lighthouse when you’re unsure, your rudder when you’re off course. When the waters of life—or dating—get rocky, you always have something strong to steer by. Some call it home; I call it Kennebunkport.
