It Happened to Me: A Craigslist Stranger Paid Me To Be His Prom Date

After a bit of cursory searching, I found the key: a poster offering $200 for someone to accompany him to his law school formal.

May 28, 2012 at 11:00am | Leave a comment

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I mean, let's be real, I'd probably do this for a lot less.

My last year in college, I was a little hard up for money. I was facing graduation with some trepidation, and my various barista / catering / caving instruction classes weren’t quite giving me enough financial wiggle-room to feel comfortable moving out West while still managing to feed myself. 

Conveniently, I have a history of being up for pretty much anything in exchange for petty cash. I once, for example, ate half of a raw onion like an apple for $10 (and, let's be honest, the attention). I'm just waiting for someone to offer me a lump sum in exchange for, say, consuming an entire bottle of sriracha sauce with a spoon.

So after a bit of cursory Craigslist searching, I found the key: a poster offering $200 for someone to accompany him to his law school formal. The law student was busy studying for the New York Bar, the post explained, but he still didn’t want to be a lone wolf hunched over the open-bar vodka tonic while his friends broke it down on the dance floor. I contemplated it for a second, then opened up my e-mail. 

“Sure,” I wrote. “Why not?”

A large part of me was definitely angling for that $200. But I have to admit: I was also stirring some pretty John Hughs-ian tropes into my personal fantasy-pot. I had visions of a high-cheekboned, painfully shy early-days Jake Gyllenhaal, who’d been too wrapped up in constitutional -- no, environmental law to find himself a prom date. If he was also nursing some sort of sexual identity crisis that could only be absolved by employing a fast-talking beard to dance with him to Rihanna, well, I was happy to help out.

It wasn’t as if I thought I would go all “Pretty Woman” on the guy. But I figured, hey, if I was gonna spend four hours with him, might as well make friends. Plus, there’s something so “young adult novel” about being paid to go to prom with someone, even if everyone present is over the legal drinking age.

Then I met him. In reality, Hugo was not the stooping doe-eyed towhead of my friendly daydreams. Hugo was a combination J.D./MBA candidate who commended me on my “witty e-mail” and sneered at the prospect of dating any of the girls in his class. 

“They’re just so…shallow, you know?” he said over our pre-prom “Ensure neither of us is a serial killer” beer. “They only want to talk about, like, what they’re watching on television or how haaaard the Bar is gonna be. They’re all liberal arts people, for Christ’ssakes.” He pulled a disdainful swig of his beer, making a disgusted face. “Idiots.”

O-kaaaay. Clearly Hugo hadn’t picked up on my 7/8s of an English degree or the fact that I’d cried for all 20 minutes of the season finale of “Parks and Recreation” the previous week. I probably should have bailed right then and there. But no one likes being called an idiot, even by someone who clearly spent so much time balancing on a self-righteous pedestal of law textbooks that he couldn’t convince anyone to go to prom with him.

“Right,” I said, changing the subject. “Let’s draw up a contract, shall we?” 

I don’t have a copy of our pre-dance contract on hand, but it basically said the following: “Hugo the Law Student (hereafter known as HLS) agrees not to pepper spray Our Undergraduate Hero (OUH) into tiny pieces and throw her into the gorge for fun. Also, this $200 will buy witty banter” (though NOT about NBC comedy, apparently) “and dancing and maybe some hair-flipping if OUH is so inclined and maybe has a whiskey ginger. And nothing else. Nothing.”

“Wait,” Hugo said when I presented the aforementioned document to him. “What about like…a hand on the waist?”

“Fine.”

“A kiss on the cheek?” 

“Fine.”

“On the neck?”

I hesitated. Alarm bells, Conway! Hypothetical quasi-Ducky of the sticky-out collarbones would have never been so bold. “…Fine.”

He leaned back, looking satisfied. “Great.”

I also had him scan his driver’s license and student ID for safekeeping. My housemates, ever the dutiful accomplices, hung them on the refrigerator with instructions to call the cops if they didn’t hear from me by midnight.

I recognize this was overkill, but I was raised on a healthy diet of "Dateline" and instinctively default to believing that everyone is vaguely out to murder me.

I’d also made a private resolution not to drink at the open bar, which is big news for a dirt-poor undergraduate. This didn’t stop Hugo, however, from pounding back the airplane bottles of vodka he’d had me smuggle into the dance in my purse. 

It was pretty fun at first, I have to admit. Because the transaction was purely mercenary on my part, I didn’t give a crap about all the gussied-up law students seeing my sweet moves on the floor. And Hugo’s friends, while clearly baffled by the presence of a strange 21-year-old encroaching on their grad school space, were actually pretty cool. 

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Dude paid $200 for four hours of moves like these. Bargain alert!

But as the night wore on and Hugo got drunker, he started pushing the limits of our contract farther and farther. Since I was in heels, he was at a prime level for “accidental” groping during the slow dances. During “Lady in Red,” and “Truly, Madly, Deeply,” he’d press his nose in between my boobs and huff in what I can only imagine was the essence of deodorant and leftover espresso residue.

He would also rub his strangely petite, now-sweaty hands beguilingly over my waist — the designated “waist area” now extended to encompass the bottom of my boobs and the top of my ass.

Somewhat luckily, I was getting over the tail end of a lung infection. Even the most vodka-fueled of law school letches lays off a bit when his date starts hacking up phlegm over his head. 

“Sorry,” I told him cheerfully, backpedaling away. “I was coughing up blood yesterday!”

By the third hour, I’d started routinely checking my phone for the time. Starting to feel seriously fatigued from my lingering antibiotic regimen and slimy from all the moist hand-on-waisting I began idly calculating how much I was making per minute. 9:13: $110 in. 10:27: $171.81. Home stretch, Conway! 

As the night was winding down, though, one of Hugo’s friends pulled me aside. He told me how great it was that Hugo had found a girlfriend and that I should really come around more often. 

“He likes you,” they said. “You should really meet his parents when they come into town for his graduation.”

Now I felt slimy for more than just the whole three hours of dancing thing. These people clearly liked Hugo enough to keep him around. My judgey-faces at his nose-groping and shaky social skills were probably excessively bitchy, I reasoned. 



This feeling of determined goodwill buoyed me all the way to the end of the night. Hugo and I bid goodbye to his friends, who insisted on taking photos of the two of us for posterity (these photos absolutely exist somewhere, but I have never seen them). I let him drive me home, which was fucking idiotic in retrospect, but I just wanted to go home and sit in sweatpants with my inhaler and "The Unusuals" on DVD. Being charming on command is EXHAUSTING.

When we pulled up outside my house, Hugo took out his $200. Before handing it over, though, he hesitated. “You know,” he said, “There’s another $100 in this for you if you let me go down on you.”

I admit, I thought about it for a second. Sensing my hesitation, he continued, “We don’t even have to fuck.”

I eyed the bills in his hand. $100 meant a lot of vegetable-purchasing potential for someone who hadn’t seen the fresher side of the produce aisle in a long time. 

Then I remembered the breach of our initial contract. If someone can’t even keep “hand on the waist” sacred, who the hell was to say that he’d stick to oral? It wasn’t even the sex factor that disgusted me -- if he’d brought it up during our initial negotiations, I might have even agreed to some casual finger-banging. It was the complete disregard for my boundaries: the assumption that if he just pushed hard enough, I would eventually concede.

It wasn’t just personally insulting; I actually found it all too familiar. It’s what a lot of men learn, I think, particularly with regard to the boundaries of women.

“Uh, no,” I said. “No thanks.”

“C’mon,” he wheedled. “Tell you what. I’ll bet you another hundred you won’t come.”

Briefly, gloriously living out my Sassy Heroine fantasies for a shining moment, I retorted, “Honey, one way or another, I ALWAYS come.” Then I grabbed the money and climbed out of the car. 

(For the record, a comeback of this badassery has never occurred to me before or since. The gods of John Hughes-bestowed idiocy had clearly taken pity on me.)

In the next week, Hugo e-mailed me several times. First, to apologize for attempting to breach our contract, which I appreciated. Then, to offer me $500 to pretend to be his girlfriend to his parents when they came to visit, which I appreciated less. 

“It’s good you look Jewish,” he wrote. “They think Jewish girls are smart.”

Again, tempting. A lot of money, plus the opportunity to reenact some truly ridiculous sitcom-style sketches, one of which would probably culminate in our accidental wedding. I thought that over.

“Sorry, no.” I wrote back. Apparently, betting on orgasms and fake relationships are my personal limit.  

I’ve never done any kind of sex work, but I imagine that there are similar issues at stake: drawing firm boundary lines, pushy customers, the occasional sense of longing for one’s Netflix while a sweaty person sniffs your cleavage. I, of course, didn’t have to face the societal stigma and very real safety concerns that a lot of sex work entails. But I still felt bizarrely vulnerable, all the same.

My date with Hugo was easily the strangest thing I’ve done for money. What’s yours?