The time: october 2008.

The place: a friend’s Halloween party at Trilogy Wine Bar in Boulder. The scene: Sarah Palins and Joe-the-Plumbers everywhere. In keeping with the election year theme, I wore a black fedora cocked over one eye, a 1940s-style blue dress with white polka dots that I’d scavenged from Goodwill, and a white satin sash draped across my chest that said “Florida.” Get it? I was a “swing state.”

5280 October 2011
More From The Issue

A friend had convinced me that this shindig would be the perfect occasion for my social relaunch; after all, how much pressure can there be when everyone looks more ridiculous than you do? I’d finally decided I was ready to date again after the drawn-out end to a tumultuous relationship left me journaling and studying corny self-help books for months. This party, swarming with young singles, seemed like a good place to start. The fact that I’d be veiled—if only slightly—made it even more reassuring. My friend played wingman in her own blue-and-red checkered ensemble with an “Ohio” sash.

I walked into the bar and immediately felt overwhelmed by the hordes of disguised revelers—a fake Jesus, a pink slip, and a guy serving wine dressed as a jug of Carlo Rossi. I contemplated my anonymity and everyone else’s. What did their outfits say about them? Was the Jesus guy suffering in some way? And the pink slip—well, at least she had a sense of humor. Maybe the jug of Rossi was a real-life wino. Only some time later would I wonder if my own costume was a metaphor for my transitional emotional state.

Toward the end of the party, as my friend and I were heading out for a slice of late-night pizza, a cowboy riding a horse (inflatable) and sporting a handlebar mustache (real) ambled over. Gesturing to his trusty steed with a tilted grin, he said coyly, “Need a ride?” Not exactly impressed, but definitely amused, I stayed to chat. Before leaving, I gave the cowboy my phone number. Why not? I’d already flirted with a guy dressed as Abu (the monkey from Aladdin) and danced with a dead ringer for Ben Stiller—I wasn’t exactly being stingy with my number that night.

I’ve heard people say that wearing a costume makes it easier to be yourself, and I agree. My swing-state facade freed me up to be goofy and carefree without feeling exposed or vulnerable. It was a rush, reminiscent of something I once read in a book about “protective anonymity…. Cast into a situation with people you never have to see again and shielded from repercussions, you turn brazenly candid.” That night, when I pulled my mask up, I let my guard down.

Over the next few months, I went on dates with other men I’d met at the party, but the cowboy was the only one who left a lasting impression. I saw more and more of him and realized how much there was beyond the mask—or in his case, the mustache. He was optimistic and independent, jovial and good-humored, honest and straightforward, intellectual and philosophical, adventurous and laid-back.

The cowboy and I have been together three years this October. Other couples have told us similar stories about meeting on Halloween in bizarre costumes. It seems as though plenty of people forget their inhibitions—for better or for worse—when they’re in disguise. In our case, it was definitely for the better. Now we spend weeks each fall trying to come up with clever costumes for that same Halloween party where we met. We might still wear masks, but now we have nothing to hide.