The hardest piece of writing I’ve ever done wasn't what you’d expect. It wasn’t a mounting pile of rewrites on a novel chapter or even a grant proposal where every comma felt like a team's success hanging in the balance. No, it was a love letter—a clutch-your-chest, lay-your-heart-bare, just-hit-send-already kind of love letter. And now, years later, I realize that writing it taught me more about relationships, communication, and yes, even myself, than any other project ever could.

Why was it so hard, you ask? Well, grab yourself a mug of tea (or wine), settle in, and let me take you through it.

Love Letters: Why Do We Struggle to Show Our Cards?

There’s something uniquely vulnerable about writing your feelings down, isn’t there? Talking, sure, that’s risky too—words spill out before you plan them, your voice might tremble—but a letter? A letter is deliberate. It's where you confess, imagine, and, ultimately, hope.

I wrote this particular letter to a person I can only describe as Alaska in human form. Rugged but tender, sharp but breathtakingly kind. We’d spent a whirlwind summer kayaking on Lake Coeur d'Alene, swapping inside jokes, and listening to The Decemberists on repeat. It felt big—and terrifying. But when summer ended, so did the casual ease of our connection. They were moving away, and suddenly I found myself with a decision: Let them go or lay it all out.

Spoiler: I went with option two. But it wasn’t exactly smooth sailing.

"Writing" on the Lake: Why Perfection Gets in the Way

Let me paint the scene for you. I wasn’t hunched over some perfect desk in a sunlit, Pinterest-worthy room. I was sitting in my old Adirondack chair on my family’s property—yes, on the lake—surrounded by my dog, a lukewarm iced coffee, and a graveyard of crumpled notebook pages.

Every draft was either too poetic (like I’d just binged Shakespeare in Love) or had the emotional depth of a to-do list. Somewhere, in my overly dramatic brain, I thought, “What if my feelings are too much? What if they laugh, or worse—pull away?” Suddenly, I was Meredith Grey, stuck in an angsty monologue with myself: Pick me. Choose me. Love me.

This is what we do, isn’t it? We edit ourselves into oblivion, trying to balance authenticity with likability. Whether we’re drafting a love letter, chatting with a crush, or navigating a tricky conversation, we want to reveal the "right" amount of ourselves. But here’s the kicker: There’s no algorithm for that. There’s only truth.

Lessons From the Lake: When You Can’t "Edit" Love

Eventually, I scrapped the drafts and opted for something radical—just…speaking from the heart. The final letter included no poetic metaphors about sunsets or obscure literary references. Instead, I wrote about The Face.

Let me explain: Throughout that summer, this person had this way of looking at me—almost like they were trying to memorize a moment. I wrote that the way they looked at me made me feel seen, loved, and safe. I kept it simple, stripped away the fluff, and just told them what I’d been afraid to all along: They’d changed the way I thought about love.

But I didn’t stop there. Because here’s the secret sauce to real connection—whether in writing, dating, or maintaining relationships: specificity. I included tiny, vivid memories—like when they fixed my kayak strap in the middle of the lake, or the way they sang along to every word of our favorite playlist. Including those moments made the letter uniquely ours, and infinitely more impactful than any flowery language ever could.

What Writing a Love Letter Taught Me About Fear

Here’s the funny thing about laying all your feelings out on paper—when you’re done, you half expect the world to shake. Instead, I just stared at the envelope, trying to psych myself up enough to send it. My mind became a greatest-hits reel of every romantic comedy disaster we’ve ever been primed to fear: Would they Ghost of Christmas Past me? Were they packing as I sat there, preparing to disappear forever?

Spoiler #2: None of that happened.

Here’s the truth: Hitting send (or slipping a letter into someone’s hands) does not guarantee a fairy-tale ending. It’s not about controlling the outcome. It’s about choosing courage over silence, about carving room for vulnerability even when the ground under your feet feels unsteady.

Like the waves on Lake Coeur d’Alene, sometimes love swells. Sometimes it fades. But the act of showing up for yourself—in all your raw, messy honesty—is a win for every version of you.

How You Can Write Your “Hardest Piece”

If I could go back and encourage past Avery as she fumbled for words, I’d tell her this: Keep it simple, make it specific, and don’t let fear decide the ending before you’ve written the story.

And so, if you, dear reader, are staring at an unsent note—or even just considering how to share a piece of yourself—here are my takeaways:

  1. Ditch the Quest for Perfection
    Your words don’t need a Hollywood glow-up (though if you’re channeling your inner Sleepless in Seattle, go for it). Imperfection is relatable—and relatable is real.

  2. Be Specific
    The little things matter. Write about the way they fold their sleeves or the one time they forgot to lock the car. Those “small” moments are often the big ones in disguise.

  3. Write for You First
    Forget the outcome. Write as a way to honor how you feel, not to get the “right” reply.

  4. Don’t Wait for Confidence to Arrive
    Newsflash: It won’t. Courage doesn’t mean you’re unafraid—it means you act despite the fear sitting in the passenger seat.

The Hardest Words Are the Ones That Matter

Let me spoil this ending for you too: Yes, the letter went well. It marked the start of something bigger than either of us had planned—but ironically, that’s not the reason it matters to me now. What I treasure isn’t the relationship it sparked but the bravery it required of me.

I think all of us have our own “hardest piece” to write—whether during a breakup, a first confession, or a moment when you realize you deserve more than you’ve accepted. The challenge isn’t just writing it. It’s trusting that speaking your truth—even when your voice shakes—is worth it.

So if you’re on the verge of spilling your heart or refolding that same piece of scrap notebook paper, take it from me: Do it. Let the words out. The world might not shake—but I promise, you will. And sometimes, that’s exactly what you need.