About five years ago, I had stupidly chosen to go to one of the most expensive colleges in the country and may as well have literally majored in Pipe Dream. I pulled it off initially by working 25 hours a week at a work-study job, but eventually, students in my program were required to get a related internship with a certain amount of scheduling responsibilities.
This was basically not a problem for most of the other kids in my school because they were Brett Ratner’s niece or, like, Michael Bay’s taint, but it posed more of a problem for me. I was sharing the floor of a 4-bedroom with my best friend, getting very little sleep on a really uncomfortable Ikea Flurm or whatever, and even that would be tight financially if I had to significantly cut down on my hours. Which I did. My mom offered to lend me some money, but she didn’t really have any and I would have felt like a gigantic sh*thead since I was the brat who insisted on going to this school in the first place.
It was around this time that I started hearing about women selling their worn underwear for money. And honestly, after you’ve worked enough demoralizing service industry jobs and are currently spending eight hours a day being yelled at by asshole publicists for getting their client the wrong rolling papers, hawking your dirty panties for $80 a pop to Philip Seymour Hoffman’s character in "Happiness" seems almost dignified.
In the stories I had heard and read about, the women used eBay to mail the panties out. But I figured, why not cut out the shipping cost and just give them to the guy? If I went on an ersatz “date” with a guy at a bar, showed him I was wearing the underwear, went to the bathroom to take off the underwear and give it to him, couldn’t I charge for the experience as well as the product? I was single, so I didn’t have anyone to answer to except myself. And, as I felt like a spoiled asshole who was paying the price for choosing a school outside my family’s price range, I had very little regard for her at the time.
I made a fake Gmail account and put an ad on Craigslist’s “miscellaneous romance” (haha, romance) that described what the process would be. I added the only picture of myself in existence where my boobs looked big. The emails came pouring in, many of them from guys who straight-up wanted sex. I only answered the ones who sounded like harmless misanthropes who just wanted to sniff some panties, not the ones who sounded like they would demand a blowjob and then murder me and reupholster their Ford Taurus with my skin.
I now realize, of course, that there is no good indication of whether someone will murder you, and I should have done this all from my apartment and paid the $5.99 shipping. But I figured that if we were in a public place like a bar the whole time, nothing bad could really happen.
Over the next few months, I reposted my ad every few days and met with 15 or 20 men to make the exchange. I bought $7 packs of cotton underwear from Target, the kind a young girl would wear. I wasn’t dating at the time -- in fact, I didn’t lose my virginity until four years after this -- and ironically, it felt like a low-pressure environment to get more comfortable with dating in my personal life. I became good at filling gaps in conversation, making the men feel at ease if they were nervous, asking them personal-but-not-too-personal questions about their lives and work. A few were married, others were single. None of them seemed especially wealthy, aside from one who wore sunglasses pushed up on his head and mansplained his stock portfolio to me.
One was a fatherly retired cop, about 55, who lectured me about the danger of what I was doing. In an effort to appease him (I clearly have father issues), I ended up giving him a cheat code: “Don’t worry! I walk around the block a few times after I leave the guy, just so he doesn’t follow me home!” Awesome.
After three vodka tonics (me), two beers (him), and 20 minutes of lecturing, I thought he had only taken the date to try to persuade a young girl from Defiling Herself. It was only when I got up to leave that he gently reminded me to go to the bathroom and take my panties off.
The other memorable one was a struggling actor, probably in his early 30s, kind of cute, who asked me on a real date. I said no. Then he offered me an extra $50 to go back to his apartment and have a drink. I said yes. (I know.) He lived in the West Village with roommates who were away. He poured me a giant glass of red wine.
“Do you want to see me on Conan?”
“Oh, you were on Conan?” He was already loading up the clip. He was a backup dancer and singer in a parody sketch of "Brokeback Mountain" where a bunch of guys dressed like cowboys sang about how gay they are. The whole thing was so surreal that my face became sort of blank, which he interpreted as awe, and he leaned in and tried to kiss me.
It was around this point that I realized things had gotten out of hand.
I’d basically made up my mind to stop then, but I had one more date after that. It was a married guy who conveniently “forgot” to bring the cash for the panties after the exchange. He wasn’t even very apologetic. I walked home disgusted with him, and myself, and how much time and energy this had begun to take up in my life. It had stopped feeling like I was getting money for panty dates -- I was getting money for absorbing incredibly sad things about the human experience. It wasn’t worth it. So I stopped.
Fun fact: After an actor cancelled at the last minute, I ended up casting "Brokeback Mountain" guy in a 3-minute short I had to shoot for class. He was playing a flasher outside a school. (Perfect.)
“How do you know him?” asked one of the boys on my film crew.
“From around,” I said vaguely.