The first place my mind goes when I think about the hardest thing I’ve ever written is back to my bedroom-slash-office during a Nashville summer so humid you could practically drink the air. There I was, surrounded by half-empty La Croix cans, my laptop glowing like a campfire in the dark. This wasn’t an article for a magazine or a ghostwritten lyric for a friend’s breakup ballad. It was a letter—an actual, honest-to-goodness, pen-to-paper letter—to my first love, years after we’d decided to break up. And let me tell you, writing that was harder than trying to parallel park on Broadway on a Saturday night.

There I sat, under the same roof where I’d once practiced harmonies with my mom and scribbled my first songs in spiraled notebooks, trying to find words big enough to carry the weight of years: love, confusion, hope, and closure. Funny enough, writing that letter taught me more about relationships (and, honestly, myself) than I could have ever learned from any how-to blog post promising “10 Steps to Move On Like an Independent Woman.”

You’d think heartbreak and writer’s block wouldn’t mix—one’s an avalanche of feelings, and the other’s a void that swallows them whole. But when the avalanche and the void collide, that’s where the magic can happen. And believe it or not, that experience reshaped how I approach every piece of writing I do now, especially when I’m tackling subjects as complicated and messy as dating and love.

Sitting With the Discomfort

Picture this: You’re staring down a blinking cursor or an empty page, and it’s like you’re waiting for it to break up with you first. That’s what it felt like every time I tried to start that letter. What do you say to someone when you’re not sure if you owe them an explanation, an apology, or just the truth? Writing that letter wasn’t about tying everything up in a bow—it was about sitting in the mess long enough to figure out what needed to be said.

Love (like writing) is inherently vulnerable, and that’s what makes it so gut-wrenching and so beautiful. Sometimes the hardest thing to do is to be honest, not just with someone else but with yourself. Eventually, I realized that the letter wasn’t about reliving the greatest hits of our relationship or finding the perfect line (though I had certainly thought up a few jukebox-worthy closers). It was about owning the uncomfortable truth that this story had ended, but it was still important.

When I finally picked up the pen, I wasn’t crafting a Grammy-worthy speech—I was letting the words pour out like steam escaping a kettle. And I learned something that I think translates to any tough conversation, whether it’s with an ex, a partner, or even your therapist: It doesn’t have to be perfect. It just has to be real.

Start With What Scares You Most

Here’s the unpopular truth: The hardest thing to say in writing is usually the thing you need to say the most. That letter? It didn’t need poetic metaphors or callbacks to happier times. It just needed one terrifyingly honest sentence: “I still think about us, and I’m trying to figure out why.”

I think back to that now whenever I start a tricky story or tackle a relationship hurdle. The easiest thing for me would have been to default to nostalgia, to paint some pretty picture of what we were and leave it at that. But that would’ve been fake—and relationships, like letters or any good article, only hold weight when the truth is what’s doing the heavy lifting.

So, here’s a tip: When you’re confronting something hard in your romantic life (or drafting an intimidating apology text), start by pinpointing what scares you most. Maybe it’s admitting you’ve been hurt, or maybe it’s acknowledging you were the one who messed up. Say it. Write it down. Stare it in the face. That little bit of truth? It’s the crack where connection seeps in.

The Art of Letting Go (Of Control)

Let’s talk about one of my least favorite parts of being a writer: knowing that once I hit “send,” those words are out there for someone else to interpret however they want. It’s a little like taking a fragile piece of your heart, putting it onstage, and hoping it’ll hit the right note.

Writing that letter taught me something obvious but oddly freeing: Not everything has to be fixed by the last sentence. As someone who grew up watching my parents harmonize over every disagreement or misunderstanding (usually with the aid of a guitar), I’ve always been one to search for resolution. But life doesn’t always work in tidy endings.

When I handed my letter to my ex—yes, handwritten and sealed in an old thank-you card because romantic clichés are my kryptonite—I resisted the urge to stick around, to manage their reaction, to steer the conversation where I thought it should go. Hard to believe, but breaking free of that control felt like the bigger act of love. Trusting someone else with your honesty, even when it might get messy, is a true leap.

If you’re in a similar boat—whether it’s an overdue conversation with someone you loved or an email that might change an unspoken “what if” into a definitive “what was”—remember that you don’t have to dictate where it lands. You can be both vulnerable and free.

Closure Is a Myth (But Showing Up Isn’t)

Here’s the kicker: Writing that letter didn’t give me closure in the traditional sense, like some a-ha moment followed by fireworks or group harmonies. Instead, it gave me clarity. It allowed me to acknowledge a chapter of my life with gratitude while still admitting that it wasn’t meant to be my whole story.

It’s tempting to chase closure like it’s a golden ticket, the thing that will finally make things feel neat and painless. But let me tell you, relationships don’t often come with closing credits. Sometimes, the best we can do is show up—whether that’s on paper, over coffee, or in therapy—and say that we cared enough to try.

If love has taught me anything (both in the doing and the writing about it), it’s this: You won’t always get the answers you’re searching for. But you will learn what you’re made of, and you’ll be better for the trying.

Final Takeaways (or Lessons Learned)

Now that I think about it, that letter really was the hardest thing I’ve ever written—not because the words didn’t come but because of the risk that came with saying them out loud. And honestly? It was worth every messy, awkward, doubt-filled minute. So here are a few things to keep in your back pocket when life calls for writing the hard stuff:

  • Honesty beats perfection every single time.
  • Say what you’re most afraid to admit—it’s probably what needs to be heard.
  • Let go of what comes after. Send it, speak it, sing it if you have to, and let the chips fall.

Whether it’s a breakup, a love letter, or standing on the edge of something new, writing teaches us the bravery to admit what matters. And sometimes, that’s hard—but boy, is it worth it.