The Hardest Piece I’ve Ever Written
There’s a moment every writer fears: the blank page staring back at you. Usually, I can ward it off with a strong cup of coffee, a playlist of moody indie folk, and some tough-love pep talks. But one assignment hit me so hard I almost gave up entirely. Spoiler alert: I didn’t. And that’s why you’re reading these words now.
It wasn’t a high-stakes exposé or a harrowing deadline that cracked me open. No, it was a love letter. Not the swooning, hearts-dotted-over-the-i’s kind. This was a deeply personal, introspective reckoning—one I had avoided for years. It was the kind of writing I knew might break me before it healed me. And it started, as so many things do, with a single question.
The Letter I Couldn’t Send
Let’s rewind to the quieter suburbs of my early Boise days. I was fresh out of college, navigating grown-up relationships for the first time. Back then, I believed love was like a good hiking trail: you pick a path, commit to it, and deal with the occasional snake or unexpected rainstorm. But sometimes, your trail dead-ends—and that’s what happened with R.
R had the kind of charm that should come with a warning label. He got along with my dad over pint tastings at our family’s brewery and could hold his own when my mom set him straight about Boise’s proper pronunciation (it’s boy-see, not boy-zee, by the way). Our relationship was a slow burn that eventually fizzled under the weight of our mismatched priorities. When it ended, I shrugged it off, telling myself I was “fine.” A classic breakup trope, right? The girl who’s not crying into her Ben & Jerry’s? That was me—or so I thought.
Years later, my editor assigned me a piece on the role nostalgia plays in romantic regrets. “Make it raw,” she said. “Readers love vulnerability.” Easy, right? Except that when I sat down to write it, I realized the only way forward was to confront the one thing I’d been avoiding for years: a letter I’d ghost-written a hundred different ways in my mind but never sent to R.
Getting Uncomfortably Honest
Writing about breakups for a living is a bit like trying to be a vegan at a BBQ—exhausting, a little preachy, and inevitably messy. You’re constantly balancing intellectual observations with personal experience, trying to sound insightful without airing too much dirty laundry. But this assignment demanded more than my usual detached analysis. It required me to write about love, loss, and the fallout of my own choices.
So I did what any writer in existential distress does: I procrastinated by alphabetizing my spice rack, called every friend I’d been neglecting, and rewatched When Harry Met Sally for “research.” Finally, I sat down with a notebook and scribbled three words: I’m Sorry, R.
Here’s what poured out over the next hour was startling—not because I hadn’t thought about it before, but because I hadn’t realized how much unfinished emotional business I was still hauling around. Writing to R wasn’t just an apology for what I did or didn’t say back then; it was an apology to myself for pretending like I had perfectly moved on. I wasn’t in love with him anymore, but part of me still lingered in the choices we made together—and the ones we didn’t.
What Writing Taught Me About Letting Go
Here’s the thing about relationships—and honestly, about life: unresolved feelings have a way of sitting in the back of your closet, much like that box of emotional baggage labeled, “To Be Dealt With Later.” And much like that box, the contents will surprise you when you finally dig them out. Writing the letter to R didn’t magically fix my regret or tie everything up in a big rom-com bow. Instead, it gave me something far more useful: clarity about why we ended and permission to leave it behind.
I learned a few things from that experience—lessons I’d like to think are worth sharing. Keep in mind, this isn’t an Oprah-style master class on heartbreak. It's more of a guide from someone who’s been there.
1. Play the Tape All the Way Through
When we think about our past relationships, we have this funny habit of romanticizing the highlight reel. We remember the great laughs in the park, the Sunday mornings making pancakes, or that one unforgettable road trip. But how often do we rewind to the arguments or the overwhelming doubts? Balance the nostalgia by replaying the full picture, not just the dreamy montages.
2. Your Regrets Are Teachers, Not Enemies
Sure, regrets suck. They’re a bad hangover of the soul, a reminder of the text you shouldn’t have sent or the one you wish you did. But staring them in the face can teach you more than ignoring them ever will. My regret with R taught me to value better communication, not just in romantic relationships but in all of my connections. It forced me to get honest about what I want and, just as important, what I don’t.
3. You Can Apologize Without Restarting
I never actually sent the letter to R. For one thing, it wasn’t for him—it was for me. For another, reappearing in someone’s life to unpack unresolved emotions doesn’t always help them. Sometimes, peace means knowing when to leave well enough alone and when to forgive yourself instead. That letter gave me a closure conversation I didn’t need to have in real life.
4. Attachment Isn’t a Failure
If you’ve ever felt like you care a little too much about someone you “should be over,” let me just say this: you’re not broken, and you’re not weak. Attachments are human. The goal isn’t to stop caring; it’s to reshape your understanding of what that caring means. R might have shaped how I loved in my 20s, but he’s not shaping how I love now—and that’s a liberating realization.
5. Writing Is Vulnerability Without an Audience
There’s a reason journaling is a favorite topic in therapy. Putting pen to paper (or fingers to keyboard) leaves no room for self-editing. Writing the letter to R helped me uncover the layers of my heartbreak, hidden under years of “I’m totally fine!” bravado. You don’t have to be a writer to do this, by the way. You just need to step into a space that doesn’t judge you for feeling what you feel.
The Best Love Letters Are to Yourself
Writing that love letter to R—disguised as an apology—was the hardest thing I’ve ever written because it was the most honest. It wasn’t about fixing the past; it was about forgiving the woman I was back then for fumbling through the confusion of young love.
Since then, I’ve come to see love letters as something far bigger than cheesy lines and bleeding hearts. They’re moments of truth—doors that can close chapters or open new ones. And sometimes, the best love letters aren’t sent to another person at all. They’re written to yourself, a little note to remind you that love, whether it ended in fireworks or in fizzling silence, left you better for having dared it.
So, if there’s a letter still lost inside you, my advice is this: Write it. If nothing else, it’ll set you free.
