The hardest piece I’ve ever written wasn’t about whaling ships or love letters pressed into the margins of an old captain’s logbook. It wasn’t about Nantucket’s fog rolling in at midnight, though I could wax poetic about that for days. No, the hardest piece was about something far less romantic: the time my editor suggested I write a guide to navigating the awkwardness of a break-up while living in a tiny, gossip-filled community—like, say, an island with fewer than 15,000 year-round residents.

Living on Nantucket has its perks: oysters so fresh they still taste like saltwater, sunsets that demand applause, and the kind of coastal solitude that lets your mind wander into great epics. But in a small, tight-knit world like this, life has a knack for becoming uncomfortably... let’s call it "intimate." Whether it's running into your ex at the only decent coffee shop or having your neighbors play Sherlock Holmes with your personal life, break-ups here come with a whole extra layer of awkward. Writing about it? Even harder.

Let’s not mince words—it was a beast of an article, and I didn’t emerge unscathed. But that challenge taught me more about connection (and myself) than a hundred history books ever could. Here’s what I learned along the way.

The First Step: Understanding Why It’s So Hard to Talk About Break-Ups

Break-ups, whether we’re talking about dramatic heartbreaks or quiet, mutual fades, are universally hard. Add the magnifying lens of a small-town environment, and it's like trying to grieve while trapped in a fishbowl surrounded by those overly enthusiastic kids from Finding Nemo.

There’s no anonymity here. “Just avoid them!” people say. Sure, Brenda. I’d love to, but my ex’s mom works at the post office, and I still need stamps. Throw in a few overly involved townsfolk—what I lovingly call the “Nantucket News Crews,” people who swear it’s their civic duty to catalog your personal life—and you can see why trying to write about the aftermath of a small-town split made me feel like I’d entered emotional Cirque du Soleil.

But here’s the thing: writing and reflecting on break-ups reminded me that the best lessons are often written in times of discomfort. When you’re forced to sit in your own emotional clutter, you begin to understand not just your relationship but yourself.

What (Eventually) Made the Article Work

It all clicked when I stopped trying to make it profound. I quit reaching for the grand, sweeping narrative about personal growth and leaned into the deeply specific, sometimes ridiculous reality of life post-break-up. That lesson carries over into how we handle our break-ups too—it’s not about spinning your pain into some Hallmark movie-worthy tale of self-discovery. It’s about getting through, moment by moment, with as much humor and honesty as possible.

Here’s a glimpse of what I shared in that piece, lessons I now pass along whenever I’m cornered at a party (which happens a lot on an island where everyone knows everyone):

1. Cry Where You Want—But Pick Your Spots Wisely

Small towns don’t let you hide. Want to weep dramatically by the ocean, Jane Eyre-style? Gorgeous in theory, bafflingly impractical when someone taking their Labradoodle for a walk stops to ask if you’re okay.

Instead, I recommend a little reconnaissance: find your empty spaces. An old wharf at dusk, the less-trafficked end of a walking trail, or even your car parked on a sandy overlook becomes your emotional HQ. Then? Let it out. Ugly crying feels surprisingly poetic with a seagull in the background.

2. Cut Off Your Inner Historian

As a history major, I’m the type who clings to artifacts and timelines. A shell collected on a first date? Kept it. A crumpled note written on the back of a brewery coaster that read, “Let’s make this work”? Tucked into a drawer. But hoarding these relics can be a double-edged sword—preserving the past sometimes anchors you there too tightly.

One night, I fueled up on too much Scottish whisky (a souvenir from Edinburgh) and ruthlessly Marie Kondo-ed the mementos. By the end, a lighthouse-scented candle had burned down to a nub, the coaster was ash, and I’d gotten a satisfying sense of closure. I’m not saying you need to torch your memories—just evaluate whether keeping them is helping you heal.

3. Own the Run-Ins

Here’s a truth no one wants to hear: you will run into your ex. Probably while clutching something humiliating, like a year’s supply of herbal tea or dog shampoo. It’s scientifically proven. Okay, not really, but it feels like it, right?

The antidote? Steal a page from the British: when things get awkward, lean into deadpan politeness and humor. When I ran into my ex at the bookstore during my coffee-fueled “all the self-help” phase, I raised a copy of How to Survive the End of the World (Or At Least Your Break-Up) and quipped, “Figured out who to thank for this one.” Took the sting right out of the moment—for both of us.

4. Find the People Who Ground You

After the original article went live, a reader emailed me with this: “It’s not the break-up; it’s the ripple effects.” That hit home. When someone leaves your life, it disrupts more than date nights—it can shake up friendships, routines, even how you see yourself.

If you feel unmoored, find the things (and people) that keep you steady. For me, it was the friends who nonjudgmentally stockpiled cookie dough in my fridge and the harbor views that reminded me life, like the tide, is always moving.

Why This Article Changed Me

Ultimately, what made writing that piece so hard wasn’t the break-up itself or even the nosiness of the Nantucket grapevine. It was confronting the simple, human fact that the end of one connection will have you asking hard questions about all the others. What do I want from love? How do I show up for others? Who am I without this person? Writing about it made me face those questions, and spoiler alert: I didn’t have all the answers.

But the process also taught me to lighten up. Romantic failure isn’t always a Shakespearean tragedy. Most of the time, it’s an awkward comedy with a dash of heartfelt drama—like tripping on a cobblestone street but ending up next to a great sunset.

Moving Forward—and the Real Takeaway

Here’s the thing: Break-ups, much like the hardest writing assignments, are chaotic but clarifying. They make you sift through what matters most and find a way to let the rest go. If you’re reading this from the middle of heartbreak, know this: you’ll make it through. Eventually, you’ll pack up the metaphoric boxes, find a new route to avoid the coffee shop if you must, and learn to laugh at the whole tangled mess of it.

And if you do live in a small town—or a small island—just one piece of bonus advice: never underestimate the healing power of ferry rides, long walks, and distracting yourself by people-watching tourists in overly ambitious cable-knit sweaters.

Because eventually, as I learned, you’ll look back on it all—the heartbreak, the awkwardness, and, yes, even the hardest piece you’ve ever written—and realize there’s beauty in starting over.