That Time I Dated — and Dumped — a Nice Guy Just to See What It Was Like

Fresh off having my heart broken for the first time, I wanted something safe and easy. I should have known that would mean breaking someone else’s heart.

Illustrations by Sophia Foster-Dimino

There was a guy who used to bring me love poems at work. We were both bartenders in New York’s East Village. Jamie would scribble silly poems on napkins, then bring them across the street and have his after-work drink at my bar. He professed his adoration of me, but the whole thing – the poems, the compliments – was so over-the-top that I thought he was gay and joking. He was tall and broad-shouldered, and almost too handsome, in a made-for-TV kind of way. But even after I realized that he wasn’t just being cheeky, and actually had a crush on me, I continued to laugh it off as if we were both in on some hilarious joke. He wasn’t my type; the fresh-faced Midwestern thing didn’t do it for me. He’d lived in New York for a few years, but was still a shiny new penny, naively hopeful, here in my hometown to follow his dream of becoming an actor. I was a snarky, tattooed, high school dropout, tending bar at one of the many dives I’d been drinking in since…