I Was a 'Hipster Hooker' (And It Sort of Ruined My Life)

How taking my clothes off for a Madam and the story that followed landed me a stalker, media scorn and ultimately taught me the value of privacy.

Aug 3, 2011 at 2:02pm | Leave a comment

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"Well, Ms. Pilot. I can't offer you $950 an hour."  

I was sitting in a folding chair, across from one of the top editors at a successful newspaper in Midtown, Manhattan, just a couple of months ago. The interview was going fairly well, until now. He had called me in to discuss a potential full-time position at the paper I’d been freelancing at for three years. He wanted me for the job or so he had expressed via email prior to the meeting. And now he was laughing to himself paying no mind to the fact that I was not.

Three years ago, just a few weeks after the Spitzer scandal broke and before call girls became a media and show-biz "trend" and overall sensation, I placed my very first feature story, “Secrets of a Hipster Hooker” in Radar Magazine.

It was a first-person account of the life of a high-end call girl. In the piece, which I spent a year researching, I not only interviewed “hip” sex workers (one of them worked at a glossy fashion magazine), but I began the story by meeting a madam who priced me at $950 (hence the reference) after I disrobed in front of her for journalistic purposes (my code of ethics was quickly dissolved in the research part of this particular story) before eventually going out on a call.

My intention as a writer was to get a feel for what my subjects had spoken so casually about -- selling sex without remorse, and liking it, too.

By pushing myself to a point of complete shame and discomfort, I discovered, fairly quickly that I was not cut out for this  when I walked away from my first, last and only outcall -- before I had even stepped inside his hotel room.

I paid for it, both figuratively and literally--$2,000 out of my own pocket for the cost of the appointment, a high price to pay for testing myself.

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At the time, the Radar piece made a big impact. But I have been working steadily since then and have written dozens of other stories since publishing it, so I didn’t expect to still be getting shit for it.

At the time the story came out, of course it was exciting. I was 22 years old and was published in a national, reputable magazine. I had worked hard on the story, and I was quite thrilled to share it. Most of my peers were interning or folding T-shirts, and I felt like I had "arrived." But after "Secrets of a Hipster Hooker" hit stands, things got pretty intense and complicated and fairly quickly.

As the story spread across the blogosphere at a breakneck pace, the scalding comments started to roll in. “Glad I got her before she became a whore” wrote a guy I had supposedly dated. "What did she master in? Seduction?" was probably the most flattering amongst anonymous snark. And then there’s the old standard when a woman writes about sex – “She only did this article to make a name for herself.” Is that a bad thing? Over the years I've broken bones, pierced my body, even boiled my skin in a motorcycle accident, but still -- the words always cut most deeply. I quietly protested by changing my Facebook status to "I AM NOT A HIPSTER WHORE."

A week after the story was out, a producer out in Hollywood phoned the magazine. He wanted to develop a TV drama based on my life – or at least my life as a “hipster hooker.” Then there was an agent who wanted me to write a book about my experience posing as a prostitute. I would receive six figures -- but I would have to "go further" and actually have sex for money. "Think about it. You'll have a book deal," he said, somewhat seductively. I declined both offers. 

I also hadn’t mentally prepared for the dejection I faced from my family. My mother was not angry, she was ashamed, which felt far worse. "What did I do wrong?" she asked. Nothing. I just happen to be the kind of daughter -- the kind of person and the kind of writer who didn't think about the big picture.

Not long after talking to my mother, I received a phone call from a restricted number, an unfamiliar and muffled voice breathing heavily into the receiver: "I'm watching you. I'm going to fuck you. Then I'm going to kill you and then [pause], well, I'm going to fuck your dead body."

The calls kept coming in, 20 times in one hour. "I need to see you or I'm going to kill myself," was the last one before I walked to the nearest precinct. The police traced the call, and 24 hours later, a 30-something successful media executive who had read about me in Radar was arrested. He spent a year doing community service, was fired from his job and to this very day, is unemployed and sweeping the streets on the weekends.

But why had I been the chosen one to receive these calls? the cops wondered. I guess when you write about sex, you open the door to all kinds of characters.

There is a saying that rings especially true in the media world. “If you want a friend, get a dog.” No guide exists to walk you through the thorny sphere of commenters and media critics. To this day, I have refused to read the vile Gawker comments. My life became like a roller coaster ride – while initially unashamed, I swiftly incurred whiplash. So I binge drank, I chain-smoked, after a painful breakup, I dated a few men and became clingy and awful. One man I ended up sleeping with even got off on calling me his Hipster Hooker. The year following "Hipster Hooker," I suppose I felt a little dead inside.

Luckily, I could take my pick of “sexy” assignments. "Work at a strip club for a week and report back." Nope. "Tell us your favorite sex positions." God, no. “Bagels?” Yes. I would write about the best bagels in the city.
 
I don't believe in harping on what could have been -- the experience made me aware, a more compassionate person, both of others and myself. But it also made me weary of literary self-exposure and much more modest than I might have been otherwise. (Some might say “boring,” but they haven’t walked in my heels.) I'm especially careful about the kinds of stories I pursue, knowing I’m not up for the scrutiny that comes along with being a young woman writing about the seedy or sexy.

So at my meeting with the newspaper editor, years later, I was feeling just as bare and vulnerable as I did in the Madam's quarters. If I ignored the inconvenient subtext behind the editor's words, I might have brushed it off, even laughed, but words mean everything to me, they always have -- and likely always will. Sure, I wanted the position, but not if I was going to be perceived as the Ex-Quasi-Hooker for Hire.

I wanted to be an open book, and I thought that posing as a prostitute, and going undercover in the seedy sex industry for a year was brave and even admirable. There is still a major part of me who is all for zipless-fuck tales, going ''gonzo'' for journalistic purposes and for no good reason at all. Yet, the allure of sharing myself with strangers was mostly better in theory. I often ask myself, could I have done this story without feeling badly in the end? I don’t think so.

I learned the hard way that if you’re going to put yourself out there, you have to be prepared to face the critics. (And for a lot of post-publication therapy sessions.) It is a relief -- now -- to be slowly outgrowing the uncomfortable keywords associated with my name. "Jessica Pilot, Hipster Hooker" is not ''recommended'' by the search engines anymore.

And maybe someday I will simply be "Jessica Pilot, Writer."