Another pirate looks unflinchingly at 40

Apr 16, 2014 at 5:00 am


The first time I visited Key West, I got busted with a fake ID at Sloppy Joe’s, a Duval Street fixture since the 1930s.

I spent the next day picking up trash, tiptoeing between sunbathing spring breakers while wearing an orange vest with the word “INMATE” emblazoned across the back. I was just a few weeks shy of 21.

This week I’m back, and I’m a few weeks shy of 40. Two decades have passed in a flash like a two-minute movie trailer, and I’m at the edge of another big one.

But even with more wrinkles and cellulite, the reminders of gravity and a few too many last calls, I’m looking forward to celebrating this birthday. Milestones give us the opportunity to stand in the moment, suspended between looking back and looking forward.

For the looking-back part, my movie trailer is a romantic comedy still searching for its ending; a jumble of the stories I’ve told about myself and truly believed along the way. I’ve been the sorority girl from a small town at a big, scary state college. I’ve been the corporate-job rebel with pink streaks in my hair. I’ve been the married girl worrying about why I can’t muster the desire for a baby. I’ve been the divorcée. I’ve been the travel journalist in bedazzled headdress on the streets of Trinidad. I’ve been the American in England digging around on a farm trying to bury a broken heart.

And in thinking about my stories so far, I’ve been more aware of the stories of others. We read them every day on Facebook — the vacations, the new jobs and the babies. Sometimes they make us compare our own tales and feel bad about ourselves. But we keep going back.

“We tell ourselves stories in order to live,” Joan Didion famously wrote. Perhaps we’d be better off if we ditched the negative first drafts and focused on finding authenticity in our chapters, which reminds me of a passage from “The Velveteen Rabbit”:

It doesn’t happen all at once. You become. It takes a long time. That’s why it doesn’t happen often to people who break easily, or have sharp edges, or who have to be carefully kept. Generally, by the time you are Real, most of your hair has been loved off, and your eyes drop out and you get loose in the joints and very shabby. But these things don’t matter at all, because once you are Real you can’t be ugly, except to people who don’t understand.


When I landed in Key West with my boyfriend Tony this time around, our cab driver offered us a snippet of his story. He left home at 17 and moved to the island 19 years ago from Honolulu. He still wore the Hawaiian shirt, though. “It’s spring break,” he warned us. “They burned six balconies off the Sheraton a few years back.”

He suggested we try the Cuban coffees near our hotel at Sandy’s, a 24-hour walk-up restaurant run out of a Laundromat.

And so the next morning, we met Julio, the unofficial greeter at Sandy’s, and heard his story. He moved to the island to heal a broken heart after his wife died. “Trying to forget,” he said. “But you never do.” He also broke his leg in a game of pool, a story I wish I’d asked to hear more of.

“What do you drink?” I asked him, looking at a menu board featuring cafe con leches and espressos.

“Tequila,” he said, showing a flask for his coffee to prove it.

Then at Blue Heaven, our bartender wanted to hear my boyfriend’s story, so Tony wound up telling a familiar one in our town.

“You’re from Nashville? Are you a musician?” the bartender asked.

“Yes,” Tony answered.

“Are you famous?”


If I’m lucky enough for future stories, I hope they include me as an occasional pie maker, a gardener, a wacky old-lady adventurer. I hope they’re filled with creative work, but I hope they put less worth on the work and to-dos and more in simply trying to be Real. I want to tell a grateful and faithful story of a friend, daughter, sister, partner. And I hope I’ll notice the good in everyone else’s story, too, staying more in the suspended position of the present without the aid of a milestone.

But for today’s story, I’m back at Sloppy Joe’s.

It’s less cool than I remembered, a tourist’s paradise, like the Tootsie’s of Key West, with Ernest Hemingway as its Kris Kristofferson. According to legend, Hemingway named the bar while teasing the owner about having a sloppy place where alcohol sloshes onto tile floors.

Standing on those floors, my story casts a woman from Nashville looking at 40. I have less money in the bank than I would have expected at this age. I’m less fit than I want to be. But turquoise water laps at boats a few blocks away. There’s a frozen piña colada in a plastic cup at my left hand, and a man I adore at my right. Blood courses through my veins and salty air fills my lungs.

And this time through the door, they didn’t even card me.