The hardest piece I’ve ever written wasn’t the one where I had to distill decades of love lessons into a 600-word feature or even my memoir, where I bared my soul to an audience of strangers. No, the hardest thing I’ve ever written was a breakup letter to someone I never officially dated.

Why is that? Because ghosting would’ve been easier. A half-hearted text? Simpler still. But writing a letter—to someone you care about, respect, even admire—feels less like breaking up and more like grief, like trying to bottle up a thousand tiny moments and explain why they can’t multiply anymore. This wasn’t casual flirtation turned sour or an easily pinpointed disaster—you know, the “he wanted pineapple on pizza” kind of deal. No, this was one of those nearly-relationships, the kind where potential loiters like a seagull waiting for you to drop your sandwich. Promising but impractical. Lovely but impossible.

Looking back, it taught me lessons not just about endings, but beginnings too. For anyone navigating complex connections or complicated goodbyes, I’ve got some wisdom to offer—wrapped up in wit and a dash of Maine-coast realism, of course.

1. When the Tide Recedes, Let It Go

I met Evan (not his real name, but let’s roll with it) one summer while guiding a tour through Acadia’s less-obvious trails. He wore a flannel shirt like it was his uniform and asked all the right questions: “What’s your favorite trail here?” and “Do people really eat more lobster rolls than sandwiches in this town?” Our connection felt like the coastline—easy, natural, beautiful. He stayed in touch after his trip, sending the occasional email about hiking in Oregon or a great nature essay he’d discovered. Over time, those emails morphed into video calls, long conversations about everything from food sustainably sourced to whether “National Treasure” is Nicholas Cage’s best movie (it is, by the way).

But geographical distance is like the ocean. It separates people in ways you don’t fully see until the water rises. Bar Harbor and the Pacific Northwest don’t exactly make for easy Sunday plans. And soon, I could feel how that distance—physical and otherwise—was tugging at us.

Sometimes, relationships fade not because anyone messed up, but because circumstances or tides pull too strongly in opposite directions. Evan and I didn’t crash spectacularly, no tidal wave of betrayal. It was more like the gradual receding of a tide, leaving behind small treasures: memories, admiration, and the inevitability of goodbye.

2. Crafting the Letter: Honesty Meets Humanity

Writing that breakup letter felt like preparing to summit Katahdin without a map. What do you even say to someone who hasn’t technically wronged you?

Here’s what I learned:
- Begin with kindness. Acknowledge the good stuff, the laughter and shared interests. People deserve to know the ways they’ve mattered, even if things aren’t working. Evan’s hiking stories and thoughtful questions helped me through a tumultuous season of life—I told him that.
- Be brave in your truth. The hardest words to write? “This isn’t working.” Not because anything broke, but because it takes courage to recognize when something isn’t right, even when it’s good. I explained how our connection felt bittersweet—wonderful in some ways, but just out of reach in others.
- End with gratitude. Leave things better than you found them. Life is not a campsite, but this principle absolutely applies to human connections. I thanked him for the journey, the shared conversations that made my world feel bigger.

Writing it brought clarity. Just like walking through a foggy morning in Acadia, things start to sharpen when you take deliberate steps forward.

3. Laugh When You Can—Even During Goodbyes

The thing about endings is, they don’t have to be all tears and melodrama. If you can, add a little levity, especially for nearly-relationships that leaned on playful connection. My letter to Evan included a P.S.: “I won’t hold it against you if you try to convince someone else that cargo shorts are acceptable date attire—but I will silently disagree.”

Humor softens edges. It turns sadness into something bearable and reminds us that life, even in difficult moments, doesn’t always need to be taken so seriously.

4. Nearly-Love Is Still Real Love

Letting go of something not-quite-yet solid feels slippery. It’s tempting to dismiss it—“Oh, it wasn’t like we were even dating…”—but that does a disservice to the connection you had, however brief or undefined. People talk about ghosting as if it’s acceptable currency in our dating economy, but honestly, I can’t endorse it. Relationships, even the fledgling ones, deserve acknowledgment for what they were: attempts at connection. And connection—flimsy, fleeting, or full-blown—enriches life.

What I had with Evan wasn’t nothing and acknowledging it was harder but far more rewarding than pretending it didn’t matter.

5. Endings Make Way for New Horizons

The funny thing about hard decisions? They open up space. It wasn’t long after writing Evan that I finally recognized I’d been holding back—staying on the coast of “maybe” because I feared the ocean of “what if.” That bittersweet letter gave me permission to turn inward, to stop drifting toward safe but doomed harbors and instead set off toward possibilities that actually fit.

In terms of dating advice, the lesson is this: if something feels tenuous, mismatched, or heavy with unfulfilled potential, you don’t have to wait for disaster to justify moving on. Sometimes, the hardest pieces you’ll write in life—whether on paper or with decisions for your heart—are the ones that set you free.

Embrace the Takeaway

There’s no script for navigating the landscape of connection. Some moments will feel like mountaintops, others like you’re ankle-deep in a tidepool with no direction out. But all of it teaches you something.

When I visit those Acadia trails now, I think of Evan sometimes—of how two people can cross paths, affect each other in profound ways, and still separate with kindness. And maybe that’s the real lesson in this hardest piece I ever wrote: letting go, whether it’s through words or decisions, isn’t always about endings. It’s about making space for new trails you haven’t even discovered yet.

So here’s my advice: write the letter. Say the things. Express the gratitude. It might be the hardest thing you’ll ever put into words, but it could also be the most freeing. And if all else fails, throw in a laugh—because cargo shorts really are where we draw the line.