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Model: Shelly Kaplan

For love or money

Sure, sex workers get lots of "dates." But finding a long-term partner? Not so easy.


Lying to your date about what you do for a living—and keeping the charade up for years. Dates who expect you to be wild and kinky, when you just want gentle, romantic lovemaking. Dates who assume you have an STI, even though you get tested more than anyone you know.

A stressful job can interfere with dating, but sex workers may have it toughest of all. The above experiences are common ones for those in the trade, not to mention the debilitating jealousy that dates or partners often feel when you make your living through sex.

“I know lots of sex workers who make thousands of dollars a week, but when they get a day off they spend it at home. They don’t have relationships or dates—their sex life is their work,” says male sex worker Dante, 23, of Logan Square, who’s been in the business for a decade.

The Sex Workers Outreach Project (SWOP) advocates for decriminalizing and destigmatizing sex work. Members have an anarchist and sex-positive attitude; they are comfortable with their sexuality and what they do for a living. They say their work has become a lot more accepted, even trendy, in recent years; but there’s still a long way to go before they can feel comfortable that potential dates won’t judge, fetishize or despise them for their erotic vocation.

“Sometimes people think sex workers are easy, that you will hook up on the first date,” says Serpent, a SWOP Chicago cofounder who lives in Pilsen and advertises her services over the Internet. “So, in my personal life, I try to be the opposite of that stereotype.”

Often sex workers have only a small number of clients whom they meet on a regular basis, blurring the lines between paid relationships and “real” relationships. Dante says his clients often become close friends. Serpent knows many colleagues who have ended up dating clients, “and I’ve always seen it turn out badly.” For her, clients are off-limits as “real” dates. “For one thing, you lose a client so you’re losing money. And it gives clients the idea that if I see this person enough times they’ll start dating me and I’ll get it for free.”

Sex workers also complain of partners who expect them to act like professionals, using a variety of toys and tricks, even when they are off the clock. “That’s like asking an accountant to do your taxes” for free, Dante says.

Some sex workers say the “lifestyle,” as they call it, is so emotionally and physically taxing that it makes it hard to have healthy, stable love relationships—even years later. More than half the female sex workers in a 2008 DePaul University study reported having romantic but often abusive relationships with their pimps.

Olivia Howard, who quit prostitution 19 years ago and now helps women leave the industry, says it can take years to develop a positive dating life. She says if a man wants to do something in bed “that would be normal for someone without my background,” it might trigger flashbacks to demeaning or abusive experiences with clients.

Angie, 30, says the low self-esteem she has felt since working as a prostitute off Craigslist has caused her to put up with cheating and abuse. She fears potential dates would look down on her once they learned about her job. “I don’t think it’s really good to date until I’m out of this.”

Serpent says that for sex workers to have a fair chance at positive dating lives, public attitudes and laws will need to evolve to the point where their trade doesn’t raise eyebrows any more than the revelation that someone is an attorney or an acupuncturist. “Come on,” she says, “it’s just a job.”

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