How Does An Escort Find A Boyfriend?
Playboy Africa|May 2021
Hint: It’s Not Easy
Tim Struby 

It was a balmy August night in New York City and Maggie couldn’t recall the last time she’d felt butterflies. In a strappy blue dress, DKNY tennis sneakers and her brown hair in a ponytail, she’d walked the 14 blocks from her apartment to the north end of Union Square, where she began scanning the crowd. It didn’t take long to find Rich. Sitting on a bench in jeans and a paisley shirt, Rich, a graphic designer, looked just like he had in his pictures: dark spiked hair, angular features, a preternaturally youthful 32-year-old. Maggie waved. He smiled. As they set off to grab a drink, the chemistry was as immediate and intense as it had been on the phone for the past week. When they got to the wine bar, he opened the door for her, wiped down the table. Compared to her last relationship—two months with a self-absorbed photographer—Rich was a thrilling breath of fresh air.

Yet even as they talked and laughed effortlessly, Maggie knew that no matter the connection, her career would be an issue. After a very religious middle-class childhood in the Bay Area, Maggie became a high-end provider, a.k.a. an escort, a sex worker—someone who charges upward of $1,000 an hour for services. The 30-year-old vegetarian is a classic beauty, an astrology-obsessed empath and she is unwaveringly proud of her profession. But as the fight for sex-work legalization builds momentum, she and her fellow providers face a more personal, constant struggle: dating, relationships and love.

Although the job perks include Michelin-star meals, first-class flights to exotic locations and cash—lots of cash—the life of a provider is often isolating. Emotionally draining. Occasionally traumatic. The nine women interviewed for this story by no means represent the vast spectrum of sex workers who engage in prostitution, a line of work that includes multiple class strata and myriad genders. Nor are they victims of trafficking or beholden to pimps. The choice to enter the business was, and still is, their own. And as glamorous as the work can be, their lives bear little resemblance to hackneyed popculture story lines.

“Mainstream society at large is able to romanticize sex workers,” says Bre, a 28-year-old New Yorker who’s been in the business for five years. “We look at [sex work] as the most beautiful, tragic love stories that ever can exist, and I hate the way all of them end: She gets saved, or she dies on the block.”

But all the women interviewed for this story made one point very clear: The longer they remain in the business, the more they tend to understand the importance of a partner. The more many of them crave some sort of relationship.

“I have a monogamous mentality,” says Maggie. “And just because we’re sex workers doesn’t mean we don’t want love any less than anyone else.”

Finding a significant other in the modern age is hard enough for anyone, let alone someone who has sex for a living. But providers are well aware of the challenge.

“It’s complicated,” admits Maggie. “You just have to bolster yourself for the ensuing battle.”

So how do high-end providers meet potential paramours? No differently than most single people these days: dating apps like Bumble, Tinder, OkCupid and Hinge (where Maggie matched with Rich). The process, however, can be tricky. For obvious legal reasons, providers rarely reveal what they do for work on a dating profile. And since the apps are relatively sparse on personal information, escorts have to navigate around men who might react poorly to their profession. Red flags range from conservative politics to pictures from church functions to anyone who appears too buttoned up. Photos from Burning Man, kink pics and other progressive alternative signals are encouraging. The most reliable app appears to be OkCupid, where members customarily provide more in-depth profiles.

“You can post questions related to sex work and get lots of good information,” says Krista, a 37-year-old provider. “You can know ahead of time if they might be hostile or unpleasant about it.”

Being a provider who’s also a woman of color can lend another level of awareness to the process of vetting potential partners. “You have this double consciousness,” says Bre. “I know that black women are hypersexualized; how does that work when you want to form a relationship with someone where you want to be your full self, but you also don’t want that full self to be misrepresented or misinterpreted? Then add on the difficulty of being a sex worker, where, by virtue of the job, you are commodifying your sexuality. It’s this really weird space, where you’re having a conversation with a partner, and as a woman you need to figure out ‘Is he a misogynist?’ And as a black woman, you have to ask, ‘Is he going to be misogynistic and racist?’”

Once they’ve waded into the dating pool, the next step is like diving headfirst into the deep end. Time for “the talk.” Coming clean with what they do for a living. “I couldn’t have someone who didn’t know what I did,” says Sara, a 28-year-old escort. She isn’t alone. Some high-end escorts tell those closest to them—friends, family—and this would obviously include a partner.

So it’s not as much if they break the news to a potential boyfriend as when. “Definitely not the first date,” laughs Maggie. “That’s way too much information. But all girls have different comfort levels.” Developing those comfort levels can take time; trust needs to build. But waiting too long has pitfalls as well. “I don’t want to be one or two months in,” she says, “then admit I’ve lied the whole time and this is what I actually do.” With Rich, their instant rapport actually prompted Maggie to tell him over text before their first date.

How then to share this information? Again, every situation and every provider varies. “I’ve tried everything,” explains Sara, who’s been a provider for nearly three years. “I’ve been blunt, I’ve been delicate. I’ve asked if they’ve seen Pretty Woman.” With one of her exes, she described herself as a “well-compensated, low-volume companion.” Maggie prefers not to beat around the bush. “I say I’m in the sex industry,” she says. “Then guys say, ‘What does that mean?’ I try to explain the job. But I ask, ‘Look, how much do you want to know?’”

Rich wanted to know a lot. He wasn’t at all like the guy who’d called Maggie a “cum bucket” when she’d told him. Or the guy who said, “You must really know how to fuck a man.” Or the guy who screamed, “You’re going to give me HIV!” Still, sometimes Rich’s inquisitiveness concerned Maggie. Regular inquiries about her clients’ dick sizes, asking if she genuinely enjoyed having sex with these men. But they worked through it. Their lives became more and more intertwined. Within a few months Maggie felt “all the bs was gone,” and they were building a foundation. She was in love.

Krista met Vic at a party in Brooklyn. They too had instant attraction. Who could blame them? The redheaded Krista grew up in a Southern California suburb, matriculated to an Ivy League college and possessed a fierce passion for politics and feminism. Vic was a tech consultant from South America, sharp and witty—that dry humor Krista adored. She’d felt so comfortable with him that on their first date she told him she was a sex worker.

“He said, ‘Okay,’” recalls Krista. They quickly became an item and Vic proved to be warm and emotionally supportive.

What Vic wasn’t, was jealous. “He had no curiosity about work,” says Krista. “I don’t think he saw much use in knowing. My assumption was he thought, I know what sex looks like.” Her theory is that certain people—herself included—aren’t biologically programmed with sexual jealousy. “You can tell if they are, fast,” Krista adds. “They try to hide it, but they still ask questions to scratch that itch.”

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