Editor’s note: This story originally ran on Playboy.com in 2020.
Being single can suck, but finding someone worth dating isn’t easy either. Now imagine what it’s like for “providers”—sex workers who are paid for their companionship and physical intimacy—who want to find that someone special. Do you tell a potential boyfriend that you sleep with others for a living? If so, how do you tell them? And when? And how do you find them in the first place? Those added layers of difficulty are the focus of journalist Tim Struby’s new Playboy feature article, “How Does an Escort Find a Boyfriend? Hint: It’s Not Easy.”
Struby, a New York City–based writer whose work has appeared in The New Yorker, ESPN the Magazine and New York, to name just a few, is no stranger to subcultures. His reporting and research often span multiple years—“I’ve done stories that take a month to a year to four years,” he says—in which he immerses himself in various underground communities, including South Africa’s illegal street racing scene and the East Coast’s mafia-connected boxing crowd.
For this particular feature, Struby spent more than a year conducting in-depth interviews with high-end escorts about their attempts at starting and sustaining long-term romantic relationships while pursuing an often stigmatized career. We wanted to know more, so we spoke to Struby about what it was like to get to know these women, what the process taught him and whether dating can ever be a walk in the proverbial park.
PLAYBOY: I’m curious about how you came up with the concept for your article.
TIM STRUBY: About five years ago a friend of mine, photographer Lynsey Addario, reached out about a multimedia project she was working on for an organization called Project&. They wanted to honor the 40-year anniversary of Working, a book by Studs Terkel about the everyday lives of working people, by talking to people from all walks of life and putting together interviews and photos of them. I had a friend who was connected with an escort, and I thought that would be an interesting perspective to include, so I had her introduce me.
When I interviewed this woman she mentioned that she had a long-term boyfriend, and later another escort told me she was married. I had never thought that was possible or even considered that reality before. How do escorts have a boyfriend or a husband? That comment stuck with me for a long time.
PLAYBOY: How did you go from thinking about that comment to writing a nearly 5,000-word feature?
STRUBY: When I look for stories, I look for something that confounds me or makes me curious. Two years later, I decided to call up one of those escorts and see if she would be interested in talking with me, in depth, about her love life. She said she would be on board. I ended up going on Twitter and finding other escorts in the New York area to interview. I reached out to about 40 different escorts, ranging from 23 to 47 years old, and heard back from maybe 10 of them.
I met up with them and explained that my article would focus specifically on their personal life and that the process would go on for at least a year—so that it would be nuanced and truthful, not sensationalized. It was a subject that a lot of them wanted to talk about but never had a venue to talk about it.
I ended up with three main subjects who were in different stages of dating—one had a long-term boyfriend, one was dating more casually and the other was just starting to navigate dates.
PLAYBOY: Did you get the sense that providing a new outlet outside their friends, therapists and fellow escorts was beneficial for them?
STRUBY: Without question. It was validating for them in a sense. Therapy is one thing, but to be in the public eye and to put this out there is another. It freed them in a way, I think.
For other sex workers who are basically celebrities, the job has its difficulties, but at least they can be open about who they are. The women I interviewed live this double life; they’re proud of what they do, but they can’t showcase what they do. I think that’s really hard on them.
PLAYBOY: You ended up working on this project for a year and a half. I imagine many stories you heard didn’t make it into the article. Did you talk to male providers or other types of sex workers like porn stars or cam girls?
STRUBY: I didn’t cover the entire scope of sex workers, because there is just such a wide range of work to cover. It would have become a book at that point.
When this story started, I had reached out to providers from different backgrounds, including race. There were a lot of similarities in experiences for the women, but I did notice in talking to Bre, a Black provider, that she had a different take as a woman of color. I wish we had more room in the piece to talk about that aspect of her experience, but we decided to focus on their experiences dating rather than their actual work.
There aren’t as many male providers as there are female providers, but I talked to one very popular provider early on in the process and I quickly realized that male escorts don’t face the same stigmas or stereotypes as female escorts. His interview was just so banal. When I talked to these women, I could tell they deal with a different beast when it comes to their dating life. It is quite possible that the men weren’t being as forthcoming with me, but overall it just seemed like their ego was built up from their work. All the women I talked to were proud of their work, but they also dealt with insecurities and issues and they were very open about talking about them. So I decided to focus on just women escorts, because I wanted to give them the most voice and the most human story.
PLAYBOY: I was surprised at how some of the women’s partners were accepting of their work at first, but their relationships didn’t work out in the end.
STRUBY: I was surprised by the same thing. You think, “Oh, you don’t want someone fucking your girlfriend. Fair enough.” But often it was less about them having sex with other people and more about time and money. That’s where it gets complicated. These women make so much money, and that can be demeaning for some men. And they sometimes have to be gone for a weekend or week at a time, and they can’t communicate with their partner while they’re working.
PLAYBOY: Did you have any preconceived ideas about this industry?
STRUBY: I came in with the idea that these women do it for a good time, but I honestly don’t think it’s all that different from being a banker or a lawyer. Their interior lives are very normal; I think a lot of readers will be surprised by that. I watched The Girlfriend Experience on Starz, and I felt disconnected from that cold aesthetic Steven Soderbergh created. It was missing all the humor that comes with this work. All the providers I’ve ever met and interviewed are so funny, smart and likable.
I have always had a soft spot for strippers and escorts because I find that they are usually more self-aware than most people. I like people who are comfortable with themselves regardless of how the mainstream views them. As a writer, I’ve talked to a lot of people, and I can honestly say I have never met more fully formed and more in-tune people than the women I talked to for this story. They came to terms with their own contradictions without hesitation. All the women I spoke to are super feminist, but they also see the contradictions in their double life. I learned an immense amount from them.
PLAYBOY: Has your own love life benefitted from this experience?
STRUBY: I don’t know if I have. Do I have a new perception about sex work? Yes. This has definitely helped me understand dating more than any dating app I’ve ever been on. But does it help with my single dating life? Not really.
PLAYBOY: Would you date an escort?
STRUBY: I don’t think I could. I just think it would be very difficult. How would you feel if you went on a date with someone, and on the second date they said they were an escort? Sometimes the providers would ask me that question, and I couldn’t really say yes or no. It’s one of those things you just do not know until you’re there. Can you share your partner? Are you comfortable with that? You don’t know until you actually experience it.
PLAYBOY: Our Playboy Plus stars, many of whom are adult actors, always tell me the funniest stories. What were some that you heard from the women you talked to?
STRUBY: One escort had an older client, around 80 years old, who didn’t want to have sex. All he wanted her to do was to come to his apartment with a fake gun and pretend to shoot him. He would use fake blood and then just jerk off to it.
The beauty of what they do is that it can be as weird and funny as that, but it can also be as mundane as a nine-to-five job. Like right now for your job, you have to sit with me for an hour and listen to me ramble on. They have to do that too. One woman would drive on the Pacific Coast Highway with a client, and he would play the same music every single time. She was like, “I’m going to kill myself.”
PLAYBOY: Most of your interviews happened before the pandemic. How has it impacted the providers’ work?
STRUBY: Because of coronavirus, their work has been shut down. However, a lot of them don’t rely on this as their sole source of income; a lot of them are in school or are doing something else. But some are getting out of the business, and some are struggling with their identity because of it. It’s hard to make that much money and be empowered and then say, “You know what, I’m walking out of here.” In a way, it’s almost like they are professional athletes with a shelf life. You can only play ball that well for so long.