“What’s the hardest piece you’ve ever written?”

A simple enough question, posed casually during a recent conversation with a friend, but one that sat with me, stubborn and uninvited, like gum stuck to the sole of your favorite sneakers. I’ve written stories that meandered for 70,000 words, essays that demanded evidence-backed arguments born of endless research, and I’ve penned heartfelt character arcs that made my laptop keyboard soggy with tears (mine, not the characters’). Yet, the hardest piece I’ve ever written wasn’t an epic romance or a groundbreaking take on heartbreak. It was a love letter—a hand-scrawled, slightly wrinkled piece of blue stationery, meant for a woman I once loved but had let drift away like a kite on a windy day.

Here’s the thing: writing about other people’s love lives? Easy. I can analyze dynamics, dissect flirting faux pas, and highlight the importance of active listening all day. But pouring my feelings into words about my own? My goodness, the difficulty level skyrockets faster than your heart rate during that first ambiguous “what are we?” conversation.

This seemingly simple exercise taught me more about vulnerability, relationships, and my own flaws than any meticulously crafted essay ever could. Let me take you through the chaos, the lessons, and—unexpectedly—the humor in all of it.

The Panic of the Blank Page

When I first sat down to write the letter, I stared at the page as though it was judging me. Blank and vast and overwhelmingly… honest. It felt more daunting than my MFA thesis. There’s no backup argument or secondary thesis in a love letter, no intellectual scaffolding to hide behind. There is only you, and the stark realization of how surveillance-camera-awkward your raw feelings can be when laid bare.

To me, the blank page in that moment was like the first five minutes of a date—the awkward silence, the quick inventory of what to say next. When writing fictional characters, the stakes feel manageable. You can conjure up witty dialogue, make them meet-cute at a jazz concert, or give them just the right amount of emotional baggage to keep things spicy. To spill your own truths? Oh no, that was like performing karaoke of a song you barely know—just a faint sense of the lyrics and that sinking fear you’ll go off-key any second.

Editing Feelings Is Harder than Editing Words

If you’ve ever edited any kind of writing—and let me flex a bit here as a professional writer—you know the art of deletion. “Kill your darlings,” they say, meaning cut the work that doesn’t serve the greater piece. It’s sound advice, sure, but when editing something as personal as a love letter? Every sentence you consider removing feels like you’re severing a limb. Do I cut the part where I apologize too much? Does that seem weak? What about the section where I admit she made the best jollof rice I’ve ever eaten—even better than my mom’s? (Yes, I wrote it. No, I didn’t cut it. Please don’t tell her.)

The truth is, writing the letter forced me to encounter a version of myself I had been avoiding. The hypercritical one, questioning whether revealing softness made me seem unlovable. The overthinker, wondering if I sounded too committed or not enough. But more than anything, I had to face my tendency to half-say things. To tuck the real emotion into subtext, as though a hidden meaning would somehow soften the blow if the letter fell flat.

Breakups (and Poorly Handled Ones) Leave Breadcrumbs

Why was this letter so hard? Because, in my case, it felt like an apology stitched into a goodbye. While a breakup can sometimes feel like yanking off a Band-Aid, my end with her had been one of those slow, spiraling fades. The distance crept in like a chilly draft under a door—subtle, then unmistakable. I suddenly wasn’t calling as often, not because I didn’t care but because my work, my fear of failure, my everything seemed to show up as excuses.

Writing that love letter made me ask: How much of the breakdown was on me? Admitting fault felt like walking outside without an umbrella even though you know storm clouds are gathering overhead. Refreshing, sure, but boy, can it soak you through.

I wrote about this. I didn’t go into unnecessary detail, keeping the letter focused on the good, the joy between us that perhaps I had forgotten to notice while it was happening. But some confessions needed to be part of the narrative. And if there’s any real-life hack I can offer here, it’s this: the courage to acknowledge your own mistakes can unburden you. It won’t magically make the lost relationship return, but it clears the clutter inside you to move forward.

Humor and Honesty Save the Day

Now, here’s the unexpected bit: In the midst of all the solemn, high-stakes emotions, humor came to my rescue—clumsy, awkward humor, the kind that sneaks out in critical moments like an emergency parachute. I admitted in the letter that I hated cilantro but pretended not to because she loved it. (That was true. Cilantro is objectively soap-adjacent, don’t debate me.) I poked fun at the time she introduced me to her boisterous cousins who grilled me on everything from my career plans to whether I could dance (spoiler: I nailed it, barely).

The humor mattered because it wasn’t just about lightening the mood. It was about showing her what she meant to me in those small, sticky-note memories that layered so naturally into my life back then. Love is in those little things, and even in goodbye, they deserve their own spotlight.

What I Learned About Love (and Myself)

Writing that letter taught me that vulnerability, while terrifying in its exposure, is where the magic lives. It’s where we tell our truths, however messy they may be. We spend so much energy constructing facades, performing confidence, and anticipating rejection that we forget the simplicity of just saying what you feel.

Here are some takeaways from writing the hardest thing I’ve ever written:

  • Admit your flaws, but don’t drown in them. A love letter—or an apology, or even an acknowledgment—needs balance. Share your humanity without self-flagellation. Trust me, no one wins when you go full drama.
  • Find the humor in your chaos. Love isn’t just candlelit dinners and perfectly timed grand gestures. It’s also shared laughter, bizarre quirks, and weird obsessions about whose jollof reigns supreme. Let that part shine.
  • Say the unsaid. Even if you think it’s too late, it’s worth it to remind someone of the ways they changed you for the better. When it’s real, it matters more than you think.

The outcome? I didn’t get the girl back. That letter wasn’t about rekindling; it was about respecting what was and letting it be, honoring what I couldn’t say during our time together. And though I sent it off with sweaty palms and a rapid heartbeat, I felt freer when the mailbox door closed.

Love Letters Aren’t Dead

So, there it is—the hardest piece I’ve ever written. A reminder that sometimes the words we struggle with most are the ones we most need to write. Whether it’s to a lost love, a best friend you’ve drifted from, or even yourself, don’t underestimate the power of a letter. As much as relationships are built in shared moments, they’re sustained in the unspoken things we dare to express.

And when in doubt? Add a dash of humor. It’s the cilantro of emotions—not everyone will get it, but the ones who do are keepers.