#TinderTuesdays: That Time I Slept With a Cross-Dresser

·Editorial Assistant

Once a week, Yahoo Style shares the funny, failed, and sometimes charming stories of Tinder dates. This week, Shelby swaps wardrobes with her date: Female, 23, Brooklyn.

I had only gone on a few coffee dates with a guy I met on Tinder, we’ll call him Jordan. They were great—the conversation flowed, there was never even an awkward beat—but I was ready to get dolled up for dinner, or at least a drink. I suggested that we meet on a Friday night for dinner, drinks, and, potentially, some other kinds of fun (if all went well).

Jordan agreed, so I prepped myself for Friday’s rendezvous: a blowout, new shoes, and $35 eyeliner. That night, he exceeded my expectations, so we barhopped through my neighborhood until we ended up at my favorite spot. Said spot’s conveniently located beneath my apartment, just in case one thing led to another.

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I wasn’t necessarily expecting to get laid (though that’d have been nice), but I was ready for this rather juvenile relationship to go one step further. Well, Jordan got drunk. Very drunk, and from time-to-time would go cross-eyed. I couldn’t figure out how I was able to hold my liquor better than a buff, 6-foot-2 climber, but I could get him into my bed. So after escorting him upstairs, I accepted that my night of fun was now a night of snuggling.

I even slept well for a few hours, until I woke up alone in bed—my biggest pet peeve! Did I do something wrong? Was Jordan embarrassed? Was he throwing up in my bathroom?

“Jordan…?” I called out.
No response.

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I dozed off again until BOOM! I jolted out of bed and found Jordan facedown on the couch in my favorite dress, my tightest dress: a strappy Herve Leger number that I bought for my college graduation. I nudged, I pushed, I yelled, but he was dead asleep, breathing heavily. Somehow, I dragged Jordan back to my room, squeezing him out of my dress.

The next morning, I told him what happened and his face turned bright red. He nervously explained his sleepwalking problem, one exacerbated by booze. I told him it was fine, no judgment. But I never heard from him again. I did, however, send him the bill for my broken zipper.

Related: #TinderTuesdays: My Date Serenaded Me With Britney Spears

Tell us about your Tinder story! Please write to tindertuesdays@yahoo.com.