The Best Worst Date Ever

I realized that, like a blackout or an overbooked flight, our shared drama had brought us together. Plus: 27 of the Worst Dates Ever.

I could tell Lena was gorgeous before she opened the door. As I stood outside her apartment, the slow, sexy version of "Stormy Weather" she was singing had me in such a trance, I almost forgot to knock. When the door swung open to reveal a tousled-haired beauty in a traffic-stopping dress, I stood stunned, saying a silent thank you to the friend who'd fixed us up.

Then everything went to crap. When I finally said "Hi," it was too late. My pause had created a conversational arrhythmia, where both people talk at the same time, then stop to let the other talk, then talk again. Our stuttering was interrupted by a scream from the next room—Frankie, her cocker spaniel, had gotten a spiky blade of grass stuck in his ear. Within minutes we were on a Mr. Toad's Wild Cab Ride—Lena crying, Frankie howling—to the vet's, where things really took a turn for the sexy when the pen I used to sign us in burst in the pocket of my khakis, creating a giant bluish stain.

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A tech took Frankie, and Lena and I sat silent in the lobby, trying to shake off the landslide of awfulness. I looked down and saw two mismatched shoes on Lena's feet. I looked up, and she was laughing, a faint trail of mucus above her lip. When I wiped it away, she nodded toward my inky crotch and said, "If I knew you better, I'd return the favor." We smiled at each other for the first time in an hour, then got quiet. Our heads started to lean in toward each other—when a very happy Frankie jumped between us, licked Lena's tears away, and peed all over her lap. We walked 20 freezing New York City blocks together, a stoned dog in our arms, unable to get a cab on a snowy Saturday night.

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Later, Lena and I sat on her couch, drinking cheap Scotch and eating stale cookies, and I realized that, like a blackout or an overbooked flight, our shared drama had brought us together. Throughout our yearlong relationship, we'd benefit from the knowledge that we had each other's flawed backs, thanks to that miserable, wonderful night. I know that dream-date fantasies have their place, but they've got nothing on cold, hard, real reality, where we see each other at our most awkward, stained, and deeply human—and still can't get enough.

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