The hardest piece I’ve ever written wasn’t a sprawling investigative article or an ambitious exposé. It wasn’t even something that required a footnote. No, the most difficult project I ever tackled was a love letter—a handwritten, crumpled-and-rewritten-too-many-times-to-count love letter. But before you roll your eyes and click away, let me assure you: it taught me more about relationships, vulnerability, and the power of authentic communication than anything else I’ve ever written.

Let’s rewind. Picture me, a couple years post-grad, awkwardly trying to date while balancing a Capitol Hill job that left me running on bad coffee and four hours of sleep. I thought I was pretty smooth—until I wasn’t. All charm and confidence seemed to evaporate the moment I tried to put pen to paper for someone I really cared about. And that experience? It was humbling. It’s also the story of why opening up is so necessary—and how sometimes, the hardest thing to say is exactly what needs to be said.

Why Writing About Your Feelings is Harder Than a Policy Memo

Let me level with you: I’ve written everything from proposed legislation to speech drafts for elected officials—and no Congresswoman ever demanded as much emotional labor as that letter did.

In dating and relationships, we’re so often sold on the idea that vulnerability equals weakness. It’s like we’re in an endless audition to seem cool, confident, and totally unbothered. But you can’t fake your way through genuine connection. Whether you’re penning a love letter, confessing your feelings aloud, or just trying not to sound like you practiced your “smooth” opening line too many times in the mirror, real connection takes effort. Messy, take-the-mask-off effort.

In neat, bullet-point form (because I can’t fully escape my Georgetown training), this is what I realized mid-letter:

  • Expressing your emotions takes courage. It’s like karaoke for your soul: terrifying at first, but sort of exhilarating once you lean into it.
  • Clarity beats complexity every time. Believe me, the five-dollar vocab I picked up in grad school didn’t help. What mattered was honesty.
  • Relatability is key. Your audience (in this case, your romantic interest) isn’t looking for Shakespeare. They want something that speaks to their heart—not your thesaurus.

The Perils of Perfectionism (or “Why Draft #7 Wasn’t the Charm”)

If you’d read my first draft—which my best friend still roasts me for—you might think I was pitching a think tank to fund climate policy, not telling the woman I liked how I felt. I was so concerned about sounding perfect that I missed the whole point of the exercise: to connect.

When it comes to vulnerability in relationships, perfectionism is often just fear in a better outfit. You’d rather throw a vague, unremarkable text into the void ("Hey, what's up?") than risk looking… well, human.

I once read that Bob Marley, one of Jamaica’s finest exports, said, "The biggest coward of a man is to awaken a woman’s love without the intention of loving her." Leave it to Bob to pack an emotional gut punch. That quote stayed with me through every wadded-up draft, because I realized the scariest part wasn’t rejection—it was the thought of not saying how I felt at all.

Channeling Authenticity: Finding the Right Words

By Draft #8, I was ready to surrender. Not to apathy, but to authenticity. I dropped the pretense, the poetic one-liners I’d cribbed from Nina Simone lyrics, and instead wrote from the gut.

It went something like this: “I don’t always have the words, but there hasn’t been a day in the last few months where you haven’t crossed my mind. I think you’re brilliant, hilarious, and the way you side-eye me when I argue that pineapple belongs on pizza lets me know you’re perfect in all the ways that matter.” (Side note: it does belong on pizza, but I digress.)

Writing vulnerably (especially when romance is involved) means exposing those unpolished, quirky parts of yourself—the ones that make you uniquely you. Think about your quirks, your unexplained preferences, and the little things that make your relationship dynamic one-of-a-kind. That’s your sweet spot.

Lessons Learned About Relationships (and Myself)

That letter didn’t just help me express my feelings; it cracked open a door to self-acceptance I didn’t realize I’d been locking. See, opening up shouldn’t be about scripting the “perfect” moment—it’s about inviting someone into your world and trusting them to show up, flaws and all.

Here’s what I can confidently say about modern love after that experience:

  1. Honesty isn’t risky—it’s necessary. I know "live your truth" is stamped everywhere from wellness retreats to Instagram captions, but there’s muscle to the phrase. Pretending to be something you’re not only delays the inevitable.

  2. Connection thrives in the specifics. The more I learned to embrace the authentic details—whether it was admitting my late-night plantain chip addiction or sharing the cultural nuances that defined my household—the stronger the bonds I built.

  3. Rejection isn’t failure. I won’t lie to you: after sending that letter, I had moments of “what if she thinks this is dumb?” (Spoiler: she didn’t.) But even if it hadn’t gone well, the act of sharing those words taught me I was capable of showing up for myself—and that’s a win.

So, How Can You Show Vulnerability Today?

Obviously, not everyone is ready to pour their heart into stationary and seal it with an envelope (if you even know where to buy stamps these days). But vulnerability comes in countless forms. You don’t have to write an epic confession to let someone in.

  • Ask meaningful questions. “What’s been on your mind lately?” beats “U up?” every day of the week.
  • Compliment thoughtfully. Instead of grabbing clichés, focus on something specific that shows you’re paying attention.
  • Admit when you’re unsure. One of the most endearing things I’ve learned is that not having all the answers makes you relatable—not incompetent.

The hardest piece I’ve ever written wasn’t hard because of complexity—it was because I had to show my unvarnished self and risk being seen. That’s never easy, but it’s always worth it.

Here’s Your Takeaway

The next time you want to tell someone how you feel—romantically, platonically, or something in between—ditch the distractions. Forget about being polished. Forget trying to impress. Instead, lead with honesty, vulnerability, and that weird little thing about you that makes you you.

Write the letter. Say the words. Take the leap. Because even when it’s awkward, nerve-wracking, or downright terrifying, choosing connection will always be the bravest—and best—thing you can do.