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Remember That One Time I Tried to Take a Male Prostitute to My High School Prom? Because I Do.

Author

Rachel Ellis

Updated on March 29, 2026

Yesterday my little sister Rebecca told me that she was promposed to.

"I think you mean proposed," I said. "No 'm.'"

"No, it's promposed. Like for prom."

"Oh," I replied, then hobbled back to my crone lair and died of old age.

Let's go back to 2004 and 2005. I was just as single then as I am now, except I was slightly chubbier, and had... actually, I guess I had a similar amount of dignity. That's alarming.

Junior Prom:

I wanted to go with this boy I was friends with, but I didn't let on because he wanted to go with this other girl. His "promposal" to her involved planting a candlelit romantic surprise scene in his basement for her to discover, which I actually, incredibly, staged for him because he had soccer practice. Which... of course he did. Like a true overachiever, I even made her a mix CD "from him." Is that the saddest thing you ever heard?

This is how I learned I'd make an awesome husband someday.

I ended up going with the boy below, a nice senior in my AP Gov class whose girlfriend was eagle-eyeing me while we posed for pictures, which is why we look the way we do below. (This arrangement only worked because he was in a different grade than me, so neither of them could attend on their own.)

Actually, it's why he looks the way he does. That's just how my face was.

All I remember about the girlfriend is that she had a big mole on the place where her chin meets her neck.

Senior Prom:

For reasons that probably stemmed from A) the story above and B) my pathological need to use humor and/or shock value as a defense mechanism so that people never suspect I have feelings about anything, I decided I would only go to senior prom if I could hire a male escort as my date. Like, a bona-fide, Brut-scented, uber-coiffed, three-piece-suited gigolo. From beginning ("Cha-Cha Slide" at 7:30) to end ("Here's to the Night" by Eve 6). I started checking out the websites of male escorts in the Tri-State area. They didn't really live up to my expectations. A lot of them looked like they might have kids. If you recall, the '04-'05 men's fashion wasn't great to begin with, and these dudes' profiles exhibited the worst of the worst: shell necklaces and thinning hair and the addressing of "women" or "womyn" or "ladies," which made me uncomfortable because even at my most charitable I considered myself "not a girl, not yet a woman." Nevertheless, I chose a few and persevered.