Sometimes, the hardest piece to write isn’t hard because of the word count or a tricky topic—it’s because it forces you to confront parts of yourself you’d rather shove into a metaphorical junk drawer. We’ve all got one of those, right? That place where you stash old receipts, bent paperclips, and emotions you told yourself you’d deal with later? Turns out, writing isn’t much different from dating: the mess you ignore is usually the mess you trip over.

I learned this the hard way when I was tasked with writing an article about love—not the poetic, candlelit-dinner kind of love. No, this was about how my West Virginia upbringing shaped my views on vulnerability and connection. You’d think it would come naturally. After all, I grew up in a town small enough that the lady at the bakery knew exactly how many pepperoni rolls my family needed every Friday (four) and where your business was everyone else’s, whether you liked it or not. But putting that experience into words? Tougher than a dollar steak.

Let me take you back to why this assignment was a battleground.

The Complexity of Storytelling: A Love Letter or a Confession?

When my editor pitched the idea, I thought, “Easy. I’m from Appalachia—home of storytelling and three-hour front porch conversations. I’ve got this.” Then I tried to write it. The first draft read like a Hallmark card: sweet, inoffensive, and completely forgettable. I tried again, this time digging deeper into what love looked like in my corner of rural America. That’s when it hit me: love in my childhood wasn’t verbal declarations or grand romantic gestures. It was welding someone’s broken swing set without saying a word, or handing over your last jar of homemade peach preserves because someone else needed it more.

In West Virginia, love was action. But as my editor reminded me (after she read draft three), love is also vulnerability. And here’s the catch: vulnerability wasn’t exactly celebrated in a place where stoicism and self-reliance were practically biblical virtues. I grew up with neighbors who could fix a car, cook a stew, and rebuild a front porch all in one Sunday afternoon—but ask them how they were really feeling, and you’d get a shrug and an offer of sweet tea.

Turns out, it’s pretty easy to write about what you’ve seen. Writing about what you haven’t let yourself feel? That’s where the real challenge lies.

Quilts and Cracks: Where Vulnerability Comes In

Here’s a little flashback for you. I once dated someone in California—let’s call her Emily—who was big into self-help books. Emily was always trying to help me “open up,” and I—channelling my inner Appalachian introvert—was about as emotionally forthcoming as a tree stump. One night, after an exhausting round of “How are you really feeling?” I did what any self-respecting West Virginian would do to cut the tension: I made her a quilt.

A quilt! Can you imagine? I thought it was the most romantic, meaningful gift ever—hand-stitched, full of stories, a real heirloom. When I handed it to her, she smiled (I’m 80% sure it was genuine). Then she said, “James, I love this. I really do. But would it kill you just to tell me what you’re thinking every once in a while?”

That moment hit me while writing the article. I could weave together stories, research, and cultural insights like patches of fabric, but none of it would matter if I didn’t let the flaws show. I had to admit that love—like that quilt—isn’t seamless. It’s full of the mistakes, crooked stitches, and patches sewn out of necessity rather than perfection. That’s the part that makes people feel connected.

Lessons Learned, Both on the Page and Off

What started as an article about love quickly became an essay on how unlearning toughness might actually be the bravest thing I’ve ever done. Vulnerability, as it turns out, isn’t about oversharing or spilling your guts on date two. It’s about offering enough of yourself to show that you care and trusting someone enough to let them see the patched-up places, too.

Here’s what I learned from that gut-wrenching assignment, both about love and about writing:

  • Let go of the performance. Whether it’s the perfect sentence or the “ideal date persona,” trying to keep up appearances only builds barriers. Authenticity isn’t easy, but it’s what people respond to.
  • Start small. Vulnerability doesn’t have to be a dramatic proclamation. Sometimes it’s as simple as saying, “I’m scared I’ll mess this up,” when you’re getting to know someone. Or admitting, “This paragraph feels like garbage,” when you’re on draft four.
  • Aim for progress, not perfection. No one’s life—or love—is a perfectly composed symphony. Sometimes it’s more like a banjo solo: a little improvised, a little messy, but full of heart.

A Field Guide to Getting Real

Whether you’re building a relationship or a career in writing, here’s the unvarnished truth: You’ll never feel 100% ready to put yourself out there. That article that chewed me up and spit me out? It hit home with readers in ways I couldn’t predict. Not because it was the most polished thing I’ve ever written but because it was honest.

If you’re thinking about how to bring more vulnerability into your relationships, here’s how to start:

  • Say the thing. Got feelings? Share them. Saying, “I really like you,” might feel cringy, but it often lands better than you think.
  • Show the work. Actions matter too. A thoughtful gesture, like remembering they love coffee with oat milk, won’t go unnoticed.
  • Don’t fear the mess. Vulnerability isn’t neat or tidy, but it’s worth it. That “messy” part? It’s usually where the connection deepens.

Looking Back, Moving Forward

That article became one of my proudest moments, not because it was perfect but because it wasn’t. Like the relationships we all try so hard to navigate, it came together in fits and starts, with more feelings than I was prepared for. But ultimately, it reminded me of something I’d long forgotten: Love—and by extension, life—isn’t about keeping your edges smooth. It’s about letting someone come close enough to see they’re jagged in places, too.

So, the next time you think the hardest part of dating, writing, or really anything is getting it perfect, remember this: It’s the messy truths and the crooked stitches that people remember most. Pull them out of the drawer. Lay them bare. That’s where the real magic happens.