Happily Ever After, Eventually

I’ve been writing romance lately.

I need you to understand how strange that sentence is. I write about thresholds and vulnerability. I’m a theater critic. I write about vigilantes and Disney World. None of this screams “meet-cute romance.”

And yet.

A couple years ago, I stumbled into Emily Henry’s books and something clicked. Then last month, I started writing a small town Hallmark-ish love story — just to see. Turns out I might be kind of good at it. The tension, the longing, the way two people circle each other before they finally land. I get it. It makes sense to me.

Here’s the problem: I have no idea what I’m talking about.

I’m 49 years old. I’ve never been in love. Not really. I’ve never had a romantic relationship that was reciprocal and healthy. What I’ve had is a pattern: I give, I get taken advantage of, I recover, I retreat and/or repeat. I’ve been the helper, the fixer, the one who makes himself useful enough to keep around. That’s not romance. That’s a transaction with worse terms. Luckily, I think I’ve learned my lesson. The hard way.

So how am I writing this stuff?

The stories I’m working on are full of damaged people — my specialty — but these damaged people figure it out. They get the happy ending. Not the bleak one I’m used to writing, not the bittersweet fade-out. The real thing.

I’ve been asking myself what makes my characters get there when I haven’t. And the answer is so obvious it’s almost embarrassing:

Someone pursues them.

That’s it. That’s the difference. In every story I write, someone looks at the protagonist and moves toward them. Not because the protagonist earned it or helped enough or made themselves indispensable. Just because they wanted to.

I’ve never had that.

I’ve also never really allowed it — I’m aloof, insular, hard to get close to. I’ve built a life where I’m helpful from a safe distance. Pursuit requires being still long enough to be caught, and I don’t do still.

When I first watched the show Heartstopper on Netflix, I wept. Not a little. I’m talking full, embarrassing, shoulder-shaking sobs. It’s a show about teenagers falling in love, and it broke me open. Because it was so beautiful. And because it felt so far away from anything I’d ever have.

I was 47. Watching high schoolers figure out something I hadn’t.

So now I’m 49, writing love stories, wondering what exactly I’m doing. Is this just craft? Am I simply good at constructing something I’ve studied from the outside? Writers do that all the time — write what they haven’t lived, research their way into authenticity.

Or is it something else?

There’s a part of me that wonders if this is practice. If I’m writing my way toward something. Teaching myself the choreography before the music starts, the way I’ve done with everything else that scares me. I wrote about pro wrestling before I ever dreamed of stepping into a ring. I studied standup before I got on stage. Maybe I’m writing romance because I’m not ready to live it yet — but I’m getting ready.

Prophetic, maybe. Or just hopeful. I’m not sure there’s a difference.

Here’s what I know: I turn 50 in five weeks. I’ve spent most of my life as an observer — watching, critiquing, helping other people with their stuff. I’m good at it. It’s safe.

But I’m tired of writing happily ever after for fictional people while I sit alone in my apartment, writing by candlelight, wondering if the thing I’m so good at describing is something I’ll ever actually get to have.

I don’t have a tidy ending for this one. No neat lesson. Just a question I’m sitting with: If I can write it, can I live it?

Kirk Sheppard is a therapist, author, and theater blogger in Cincinnati. He turns 50 in March, and he’s writing about it all year. Go to kirksheppard.com for more.