The Reality of Dating a Sex Worker Ever wonder what it's like dating strippers, hookers, escorts, cam girls, and other sex workers?

I’m now in my late 30s, and I’ve been single and dating for much of the past decade. Because of my personal story, I attract a lot of counterculture and fringe people. This includes sex workers.

Sex work is interesting in that a lot more people get involved in it than you think. Just like any hobby, job, or side hustle, there are people who dip their toe in every once in a while. Some try it once for a couple of months and give up. Others make it a career.

I dated and lived with a career sex worker for a couple of years. We’ll call her Hortense. Although that isn’t her real name, she definitely looks like a Hortense.

Hortense is a career stripper who worked in Chicago, Las Vegas, Phoenix, and traveled much of the country working some of the biggest strip club markets in the world.

She worked private parties for A-list Chicago celebrities like R Kelly and Twista. She worked the Vegas strip clubs during massive events like CES International and the AVN porn awards. She knew every corner of the industry.

You would think I met Hortense during one of my Vegas trips or at a marijuana conference. While I do enjoy my time in Sin City, I’m not a fan of strip clubs. Besides, Hortense would never have dating me if I met her there. She loathed men.

Strip clubs are pits of commerce – the girls are highly trained in the art of conversation. And they’re hustlers – it’s all about the money. The more interested a girl is in you, the more of your money she wants.

I knew this going in with Hortense and I did still let her break my heart. It’s because I let myself forget the cardinal rules I’m about to teach you.

You see…I didn’t meet Hortense the career stripper. I met Hortense the “artist.” She looked like your quiet aunt, and she’s an expert at keeping her home and work life separate. In fact, she was good about compartmentalizing everything to ensure you only dealt with her in isolated one-on-one environments. This is why I go out of my way in this blog to obscure facts she told me about her to protect her identity.

Hortense and I fell for each other very quickly, and were in a very close living arrangement within weeks. Here are the important lessons I learned.

1. Sex Workers Are Just Like You…

You want to think strippers, porn stars, hookers, and other sex workers are sex-starved and willing to fuck everyone. I’m sure that type of person is attracted to the industry, and any career requires a certain level of passion.

However, when you meet sex workers in their personal lives, they typically give absolutely no indication that they are sex workers. They go out of their way to dress down and unsexy (while still flattering and well-kept) in public. At home, they’re practically bums and can go days without showering.

When your appearance is necessary for work, you simply don’t care about it while at home. Hortense often wore sweats and clothing that made her body look pear-shaped and awkward. But she still had fake tits and 10-inch+ heels that made her nearly as tall as me at 6’2 at work. You’d never know she was the same person.

She knew how to be sexy when she wanted, but what Kristin loved about me was that I didn’t care what she looked like. In fact, that’s ultimately what caused our breakup, which we’ll discuss a bit more in later sections.

2. Sex Work Has Hierarchies…

For the first few weeks we dated, Hortense’s stories of her past revolved around her ex, who was also named Brian. She talked about how abusive he was and built him up to be a horrible person. She also cried when admitting that she was married by 21 and her ex-husband tried to shoot her in her sleep. Every story she told was about how everyone else caused the problems in her life, a theme she would later implement on me.

When she finally broke down and admitted she was a stripper who dated bouncers (both were key facts that clearly broke up previous relationships), I was initially shocked. She knew all the artist lingo, but I was noticing subtle signs that she never actually worked as a freelance visual artist. She never worked a day of her life outside the strip club – she depended on men for money for a living, and that was just her life.

I asked her about her actual career, and for the sake of continuity, I’m including information from throughout our relationship, as time helped decipher what was real and false from her stories.

Reputable strippers working at reputable strip clubs don’t typically have sex for money. They may occasionally have to blow or fuck the owner or manager (one of whom always acts as the DJ too) when they’re in trouble, but overall, they always have a choice of who to sleep with.

In some clubs, hookers are frowned upon by the dancers. I’ve heard porn stars, strippers, and hookers all have criticisms of the other industry. Each draws a different moral line, although the lines get blurred fast, especially when drugs and alcohol are involved.

Even within a club, a new girl gets “new girl money” but sticking to one club for a period of time guarantees money from “regulars.”

Eventually Kristin shut down and stopped talking to me about her work. That’s when I knew I lost her forever. She saw me as just another mark.

3. Sex Work Is Like Any Other Work…

Sex work is work, and that means it comes with all the politics of other jobs. There’s no type of work that you can do that gets you completely away from office politics, and sex workers will tell you their job is like any other…

Which it is and it isn’t. The reason Kristin fell into sex work was because she knew she could make $300-$10,000 in one night, pay her bills, and sleep and be lazy for weeks or even months. She took extravagant vacations and overspent her money. She was lazy and, now in her late 30s, she’s painfully aware of how little translatable job skills she has.

During our time dating, Hortense tried (and failed) to start an online art shop, become an art consultant, go back to nursing school, and so much more. It started to become clearer and clearer to me that she didn’t have any work ethic, so I recruited her to help me with my holiday gift guides.

Kristin made a million promises, but she failed to deliver on any of them. She was just a talker who knew how to bullshit her way through conversations and make you believe her fantasies. I dumped Hortense for dropping the ball on my career.

It became clear through working together that Hortense couldn’t work as a photographer. Instead of finishing my gift guides, she simply stole all the fancy, expensive stuff, leaving me to explain what happened to PR reps.

4. Sex Workers Sell Lies – Not Sex…

The hardest part about dating a sex worker isn’t that they work in the sex industry. It’s not the sex that’ll get you – it’s the lies.

Hortense tells guys whatever they want to hear. She agrees with everything, and she spends her time listening to people talk about their interests so she can parrot it back to the next guy. It’s a way of life.

When people ask her real name, she gives them a “real” name they’ll believe. She’s intentionally vague about what she does and who she does it with. Where she’s from always changes, so you can never quite tell what is her real life and what is just the empty fantasy she’s selling you.

She avoids giving details, and when she does, they’re white lies. “Work” is a default for however she’s spending her time that she doesn’t want you to know.

Everything I said and did with Hortense was just a fantasy she built in order to mooch off me and take half my income and resources for a year so she didn’t have to work. I paid her bills, she used my wifi, and she had full access to my life. She promised heaven and delivered only hell.

When she admitted to me she was a stripper, it was only because she had to go back to stripping. She was used to telling guys it was something she did temporarily in the past. She wouldn’t have told me if we weren’t living together.

Some women do have a temporary past in stripping. Hortense clearly had been to this rodeo way more than I had. She was a lifer, and I dated her for over a year and a half knowing what she did.

Women who can’t pull themselves out of the sex industry find it harder and harder to do so as they get older. It’s a painful lesson I learned trying to carry Kristin on my back.

5. Sex Isn’t a Big Deal

Even knowing she was a stripper, my relationship with Hortense was normal because I didn’t care. How she made her money wasn’t any of my business, and I was fully aware our relationship was tit-for-tat.

In order to spend time with Kristin, I was willing to spend some money feeding her and helping her with basic adulting. Hortense’s biggest hangup was being seen as an independent adult while she’s leeching money off her family and wealthy old men she’s sleeping with.

The sex industry itself wasn’t a big deal, because ultimately I know what customer service is like. Customers suck, and I was never afraid she’d leave me for a customer.

After I broke up with her, she started sleeping with the bouncers again (and in all reality, she probably was while we were dating). She went back to her full-time sex-worker life because she didn’t know anything else. She didn’t know how to be the person her loved ones wanted her to be.

She knew sex was important to keeping a relationship – we both did. But sex was not what made me dump Hortense.

I dumped Hortense because she knew how important my career is to me. She listened to men for a living, but she apparently wasn’t listening to me. I trusted her with the simple responsibility of earning her keep, and she tried to lie to me and convince me she did the work.

Hortense was so used to playing people against one another that when it was just me, she didn’t understand that obviously I know when I’m spending 12 hours covering for work she didn’t do. It sticks out.

Hortense has the work ethic of a child and never had to face adult responsibilities. That’s why I dumped Hortense and cut her out of my life.

I don’t have anything against Hortense. I actually like her as a person. It’s my own fault for wanting her to be something she wasn’t. I sincerely hope her the best, and I hope I answered your question, dear reader, about what it’s really like to date a professional sex worker.

I would definitely date another stripper or sex worker, so long as they had a legitimate hustle and weren’t just looking for me to carry their dead weight. If you must date a sex worker, find a temp, not a lifer.


Dr. Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer. You can find his work in Cracked, High Times, HuffPost, Lifewire, Forbes, Fast Company, and dozens of other places, although much of it is no longer under his name. Dr. Penny loves annoying fake media.

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