The air in Nantucket has a way of coaxing out the truth. Maybe it’s the salt spray, so unrelenting it feels like a bracing slap to the face. Or maybe it’s the way the island’s horizons—so vast and endless—force you to confront the hidden depths of yourself. Believe me, I know. Because for years, I fought a battle I never wanted to admit to anyone, least of all myself.

The fight wasn’t some swashbuckling maritime duel worthy of a Melville novel. No, this was more like one of those low-grade storms that roll in and refuse to leave—quiet, persistent, and utterly exhausting. My battle was loneliness. And it’s honestly wild how long I managed to conceal it, even living on an island barely thirty miles from end to end.

The Island Mirage: Loneliness in Plain Sight

Here’s the thing you need to know about growing up on Nantucket: it is achingly beautiful but also isolating in ways that seem poetic… until they’re not. I learned early on how to make a good show of being "fine." My default mode was a sort of coastal contentment—windswept hair, wistful gazes out to sea, maybe a well-timed quip about the old days of the whaling industry. People assumed I had life figured out, and for a while, I went along with it.

But underneath the charming islander façade, there were long stretches where I felt more marooned than any shipwreck survivor. I could be surrounded by people—tourists flocking to my parents’ inn, crowds at the Saturday farmers’ market—and still feel like I was floating in open water, no land in sight. You’d be amazed (or maybe not) at how easy it is for loneliness to blend in, camouflaged beneath some weathered sweaters and a “busy” schedule.

It was during one of these stretches—long winters after college, when the island shuts down to all but the hardiest locals—that I started realizing how much of my life revolved around not being truly seen. I was the guy with the listening ear, the encouraging words, the pub trivia answers (any 19th-century maritime history question, I’ve got you). But I was also the guy keeping the best parts of myself locked up, scared to show anyone what was really going on.

The Flirtation That Turned the Tide

And because life has a knack for irony, the change started with something hilariously small: a flirtation over antique maps. (Yes, I’m aware I sound like a Downton Abbey character.) She was visiting the museum where I worked—kind-hearted, sharp-witted, visiting Boston briefly on a research trip. I made some half-joking comment about her taste in cartography being “surprisingly Old World,” and for the first time in ages, I felt a spark. Not just of attraction, but connection.

Now, this isn’t the part of the story where I tell you she and I sailed off into the sunset. This is not a romantic comedy set on a cobblestoned island street (though honestly, that’d look great on Netflix). What that conversation did, though, was nudge open a door I’d kept bolted shut for years. I realized I wanted more of those sparks, more of those unguarded moments where I showed up as my whole self—historical quirks, emotional baggage, and all.

Setting the Stage for Connection

Here’s what I learned as I slowly worked through my loneliness. Being seen—truly seen—is not about waiting for others to stumble upon the “real you.” It’s about being willing to show the messy, wonderful, complicated parts of yourself in the first place. And yes, I know that’s easier said than done. So, here are some guiding stars that helped me navigate those rocky waters:

1. Get uncomfortably clear on what you’re avoiding.
I realized a lot of my loneliness came from being in “safe” roles—historian, jokester, innkeeper’s son—but rarely letting people get to me. What are you hiding behind? Is it overbooked schedules? Social media? The world’s thickest emotional armor? Pinpointing that is the first step.

2. Take micro-risks with people you trust.
Self-disclosure doesn’t have to be a grand, shout-it-from-the-rooftops kind of deal. Share a little more with a friend you already care about. Mention that fear you’ve never said out loud. Introduce them to the weird passion project you’ve been hoarding like a private treasure chest. Start small.

3. Rewrite your internal story.
Probably the biggest shift for me was realizing that loneliness didn’t mean I was "failing" at relationships. Sometimes it's just a signal—not that you’re broken, but that you want and need more connection. When I started viewing my loneliness as a compass instead of a shameful secret, everything changed.

Ending the Battle Without Giving Up the Fight

I’ll be honest, fighting loneliness isn’t a one-time victory. It’s not like one morning, I woke up, stared out over the Nantucket Sound, and declared myself cured. But what has shifted—dramatically—is how I handle it now. I’ve learned to let people in sooner. I’ve learned to forgive myself for the days I still retreat into my quiet, sea-glass moments. I’ve learned that loneliness, like the tides, ebbs and flows, but it doesn’t have to pull me under.

So, if you’re feeling marooned in your own secret battle, take heart. The fight’s worth waging, and the beauty of life is that no shoreline ever stays out of reach for long. Lean into those small, brave moments of letting yourself be seen. You’d be astonished by how transformative even a little willingness can be.

And, if nothing else, don’t be afraid to answer life’s flirtations—even the nerdy ones about antique maps. Trust me: the spark you uncover might just help light the way forward.