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 Kristin, although that isn’t her real name.

Krzystan 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 Kristin 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, Kristin would never have dating me if I met her there.

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 Kristin, 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 Kristin the career stripper. I met Kristin the 35-year-old artist. She looked like your quiet aunt, and she was 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.

We 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. Kristin 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.

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, Kristin’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.

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.

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.”

3. Sex Work Is Like Any Other Work…

Sex work 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, Kristin 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 Kristin for dropping the ball on my career.

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.

Kristin 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.

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, but it’s always in the range of Michigan and Chicago.

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 Kristin 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.

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.

Some women do have a temporary past in stripping. Kristin 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.

5. Sex Isn’t a Big Deal

Even knowing she was a stripper, my relationship with Kristin 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. Kristin’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 knew sex was important to keeping a relationship – we both did. But sex was not what made me dump Kristin.

I dumped Kristin 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.

Krzystan 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.

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

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.

But I sincerely doubt I’ll find one of those unicorns…


Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer.

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