Ask Dr. Nerdlove by Harris O'Malley

Can I Date As A Sex Worker?

DEAR DR. NERDLOVE: I’ve been reading your articles for a few months now, and you strike me as a very down-to-earth person who’s got good sense. Truth is, I need your advice.

I’m going through my own transformation from person I hated to person I want to be, and thanks to a lot of work and some therapy, I feel like I’m ready to try dating again. In a sense, I’m doubling down, because I’m also trying to rebuild my social circle from being full of people who were emotionally draining (if they didn’t outright take advantage of me), to having healthy friendships with people who share my interests. (Which is geek stuff, which is why I’m here, although my question doesn’t really have much to do with my status as a geek girl).

I’ve some success with online dating sites, and responding to Kijiji ads looking for new friends, but I’m finding that I’m running into a problem: my job. I’m a sex worker. Technically, I’m *that* kind of a masseuse. 

I know full-well the stigma around the sex trade, and, since I have no intention of remaining in it forever, I’ve managed to justify to myself fudging facts to my family and remaining friends-from-before. The thing is, even if it’s just a short term relationship or “just” a friendship, I don’t want to have to lie to people. I try to be an honest person as much as I can.

But I’m also afraid of the preconceived ideas people will have of me, and I’m not willing to leave my job: it was the first thing that got me started on self-improvement, and it remains a good fit for my personality and (current) goals. It’s emotionally fulfilling in ways that any other job I can get until I graduate university just aren’t. 

So, my question: do you have any suggestions for how I might broach this to the new people I’m considering letting into my life? Should I even, given the social ramifications? Or should I really be waiting until I’m done with this part of my life to try to build up a social circle I can be completely honest with?

Hoping For A Happy Ending

DEAR HOPING FOR A HAPPY ENDING: There’s a societal stigma around sex-work to greater or lesser degrees, depending on the precise kind. Pro-dommes, for example, carry a certain level of edgy acceptance; telling people that you’re a professional dominatrix may get you some side-eyes and muttered comments from the Wall Street set and uninvited from  the country club cocktail party, but in the more bohemian artist/musician/writer subcultures, people tend to take it in stride or even accord it a level of respect. Same with sexualized performance like burlesque or fetish modeling – it’s not “polite society” to be sure, but there’s a gritty sort of glamour that comes with it. Even certain porn stars get accorded greater level of societal approval – Stoya, Sasha Grey and James Deen are all lauded for bringing porn into the mainstream; people see them as performing kabuki theater rather than prostituting themselves for an audience’s gratification.

Of course, all of this changes as soon as someone’s exchanging money for orgasms. Stripping is still seen as “dirty” or low-class, with dancers stereotyped as desperate single mothers or brainless bimbos with daddy-issues. Escorts are just barely a step above  drug-addicted street-walkers but still seen as “fallen women”, under the assumption that no woman would willingly choose such a profession. Same with masseuses providing full-body sensual massage or happy endings; because they’re handling a client’s junk and getting paid for it, their job becomes a commentary on their morality, their upbringing, their social class and their sexuality… even if they’re perfectly happy and well-adjusted.

There is a whole host of class and gender issues bound up in sex work as well. The porn stars who achieve mainstream acceptance are held in the same social sphere as other actors; they may not be millionaires living in mansions, but they’re accorded much the same status all the same. Nadya Suleman and Sydney Leathers, on the other hand, get treated alternately as D-list celebrity or as objects of mockery (depending on which direction the blogs feel like taking today) and get called “trashy” for having chosen sex work. A former escort gets fired from her job as a teacher when someone discovers her past, but high-profile clients of escorts like Dick Morris, David Vitter and Eliot Spitzer get to skate by with a wink and a nod with their integrity intact after getting caught.

Even as sex work has been popularized in media – Billie Piper’s turn in Diary of a Call-Girl, for example, or Nicole Kidman in Moulin Rouge and Sasha Grey in The Girlfriend Experience, the narrative is still that sex-work is inherently incompatible with a romantic relationship. Hell, there’s even  a show on Lifetime – f

king Lifetime!!! – where Jennifer Love Hewitt is in a position similar to yours… and of course, the show’s drama revolves around the never-ending question of “how can she find a man when she’s the Boner Whisperer?”

Even in Firefly, where Companions are honored, even revered by society, love is taboo to them because reasons. Almost every time, the courtesan, the escort, the Companion is told to make a choice – continue as a sex-worker or enjoy blissful (and by implication, vanilla) monogamy for the rest of her life. It makes for a dramatic tale, but it tends to continue the stigma against sex-work and treats it as an exercise in “othering”; sex workers are not accorded the same opportunities until they give up their sinful past and join mainstream society.

You’re in a tough spot, HFHE. On the one hand, you’ve found sex-work to be empowering and emotionally fulfilling and it’s clearly been a positive experience for you. Maybe it’s helped you feel more ownership over your own sexuality and your desirability. Maybe it’s made you see yourself in ways you’ve never imagined or pushed you past personal limitations you never thought you could exceed. So of course you don’t want to have to hide that part of your life, and it’s unfair to demand that either you quit before you’re ready or face life as a social hermit until you do.

At the same time however, there’s still that massive social stigma. Even among people who are pro sex-work, that perceived opprobrium can be a high bar to clear; they may be in favor of sex work in theory, but they start to get squirmy with the idea of telling their nearest and dearest what their significant other does for a living. It’s the Madonna/Whore complex, only with literal whores.

Now, how do you handle this?

The obvious answer is “well, quit being that kind of masseuse”, which isn’t exactly helpful. It implies that you should be ashamed of what you do and that by implication, you are undeserving of love and affection until you have cleansed yourself of your “sins”. And quite frankly, waiting for society to catch up and get past it’s Calvanistic roots with regard to class and Victorian views on sexuality means that we’ll all be old and grey before you’re “allowed” to date and be open about who you are without judgement.

So here’s what I suggest.

To start with: let yourself date and make new friends and be open about who you are and what you do. But be selective about who you choose to let into your life and know the truth; it’s an unfortunate reality that being – or having been – a sex worker can close off a lot of avenues for you professionally and a pissed-off ex can f

k you over big time if they decide to forcibly out you.

I understand not wanting to live as though this were something to hide and be ashamed of; at the same time, it can be a lot to drop on somebody early on. I would suggest a gradual outing – not on the first date or hang-out, but before you actually have sex (or similar platonic emotional milestone with friends). You can feel things out a little to get a feel for how your prospective beau will react – and let him get to know you rather than some imagined stereotype – before explaining to him that you want to be open about your job. Just as getting to know gay people helps break down homophobia, getting to know you will make it harder to hold onto preconceived notions about sex workers. There will be some cognitive dissonance as they try to process what they think they know vs. what they do know. Sometimes the reality of who you are will win out. Sometimes they won’t be able to let go of the idea of the “fallen woman” or that only “certain types of people” do sex work.

When you do lay it out there, explain it like you did to me: that you enjoy it, that it brings you emotional fulfillment and how it’s helped you become who you are today… presumably the person that he likes hanging out with and possibly seeking a relationship with.

And then you wait. They may have an immediate reaction and reject you on the spot; it’ll suck, but it will be better in the long run because you’ll have confirmed that you two simply weren’t going to work before you became too emotionally invested. Better to cut him loose early than to have a relationship go down in flames further down the line. They may be cool with it initially but have a harder time the more the reality of it sinks in… not just what to tell their friends and family but the image of you with other guys. That can be tough, even for poly couples or people used to non-monogamous relationships. They may be a little nervous or jealous or insecure – which can be true of any relationship – and you’ll both have to be able to communicate openly and honestly with each other without fear or recrimination.

Some people may have problems with it but be willing to learn or to try to accept it. They’ll have questions; answer them as best as you can and direct them to other resources out there. Kitty Stryker, for instance, has a good article about how she and her boyfriend balance her role as a sex-worker and their relationship. Kendra Holliday writes about her experiences as a surrogate on her blog as well.

Also, you will want to hone your Spidey-sense to perfection too. There will be people who initially seem ok but are just not. You’ll find the White Knights who will think that you need to be “rescued” from your job. There will be the Holy Ones who feel like they have an obligation to save your soul and the people who think that by doing sex-work you’re setting women back. You’ll find the chauvinists and misogynists who will think that sex-work lessens you and will try to treat you accordingly. There will be predators who will try to leverage your job and your desire for privacy as a way to try to control you and abusive or vengeful s

tbags who will try to f

k you over by outing you to everybody.

If and when you do tell your family… well, there’s probably going to be drama as well. And honestly, this is one of those areas where I think you’re allowed to fudge things. Your parents don’t want to know the nitty-gritty about your sexuality and in a lot of ways, your job is tying into it. So yes, I think it’s not a bad idea to just let them think you’re a massage therapist or what-not, even if it’s uncomfortable for now.

I won’t lie to you: it’s going to be difficult. There will be a lot of people who will self-select out of a relationship with you – romantic or otherwise – because of the stigma. And even the ones who do accept you will have a hard time; there will be a lot of “who’s allowed to know what?” drama, especially if your new friends mingle with your old ones and the potential for your family finding out is high. It will be stressful. The more people who know, the more you’ll run the risk of word slipping out and having to deal with the aftermath.

So it will be tough. And you’ll wonder whether the benefits the job brings you are worth the stress that keeping the secret causes.

But don’t ever think that you aren’t worthy of love and friendship because of what you do.

However, Since I only have an outsider’s perspective when it comes to sex work, I felt bad about leaving this letter here, so I reached out to Mistress Matisse – professional dominatrix, sex work advocate, writer and columnist at The Stranger to see what advice she might have for Hoping For A Happy Ending. Mistress Matisse was gracious enough to write back.

Take it away:

My name is Mistress Matisse. I’m a professional dominatrix, and I’m also a writer and a sex work activist. Dr NerdLove was nice enough to invite me to comment on a letter he received about social life as a sex worker, and I’m pleased to do so.

Before I address this letter and Dr NerdLove’s advice, I have to say something about how he framed it, because I to make a point. The idea that you’re generally sympathetic to sex worker issues comes across here, Dr NerdLove, and that’s really cool.  However – and correct me if I am wrong – it is my understanding is that you are not, yourself, a sexworker? Obviously, how individual sexworkers experience our lives is unique to each of us, so no one sexworker speaks for everyone, including me. But – if someone has never been a sexworker, I would strongly encourage them to not discuss exactly what levels of stigma sex workers deal with, and how people treat us, in a way that suggests deep personal familiarity with such experiences.

Now that I’ve lived up to my name by topping the blog author a bit… I would pretty much agree with the advice he gave this reader. Here’s what I would say to her:

No one likes to lie, and sex workers should not have to. I’m glad you like your job. I like mine too, and our profession should be considered as honorable as any other. People who work for the IRS don’t have to lie about what they do, right? Nor do lobbyists for the banking industry, or parking-enforcement officers. And sex workers make people much happier than those professions.

But in the real world – it is an issue. If someone has just met you, and in the first hour of your acquaintance, you tell them you’re a sex worker, they are going to make snap judgments about you based on that. It’s just a fact. Very occasionally, people say something like, “Oh wow, what a cool, interesting job that must be!” Usually not, though. Neutrality is the best one can hope for in that circumstance, and a lot of the time, they are going to have a negative association with the industry. And you can’t un-ring a bell. Once the information leaves your mouth, it’s out there, and you cease to have control over how people react to it and who it will be repeated to.

So, some people want to be out as a sex worker to everyone, all the time, and that’s great if they are comfortable doing it. But it’s not everyone’s business to know what you do. Just because someone is nosy does not mean they are entitled to personal information.  Let them get a job for the NSA if they want to snoop!

It’s not usually required to speak a lie, if your conscience is finicky about that. One can just be vague. I’ve often done that with people who were just casual social acquaintances, because I simply didn’t wish to deal with their feelings about my job. Frankly, most folks are not on fire with curiosity about what just-met people do for a living anyway. They’re simply making polite conversation. It’s usually easy to make a noncommittal reply and brush past the question. In this case, you have a good cover story – you’re a massage therapist. You can stick to that, and just make it sound as boring as possible. I wouldn’t weave a lot of fictions that you’ll have to remember later – vague and boring is the way to go.

What do you do when you do feel you want to disclose this part of your life to people you’ve become close to? Well, reading stories and advice about how to come out as not-heterosexual can sometimes be helpful in deciding how you’d like to frame this discussion. I myself think it’s best to begin any disclosure narrowly. Here’s a quick example of what I mean by that: “There are times at my job when people want me to touch them sexually, and if I feel safe and comfortable doing that, then I will. I’m feeling nervous about telling you that, because I know some people think that’s not cool. But it’s not a negative thing with me, so I hope it doesn’t weird you out.” Using global-concept words right off the bat, like “sex work” or “prostitution”, can sometimes cause a knee-jerk negative response that taints any future conversations. I see that you’re positive about the role sex work plays in your life and I am happy about that, believe me! So this is not about being ashamed, it’s about taking time to build trust with someone. Keep the stakes low at first – disclose a little, see how that works. Then you can make deliberate and conscious choices about whether you want to disclose more.

This is the part where I advise you to be careful at first of giving out any information that could link your everyday-world self to your work-self. I myself have not had trouble with being outed or stalked by ex-friends/lovers, so it’s not a given, but it does happen. It’s safest to withhold work-names, addresses, websites, phone numbers, details of when and where you work, how you screen clients, et cetera, until someone has really demonstrated themselves worthy of trust. Also remember that any friends who do know must be very clearly and carefully cautioned about not accidentally letting something slip to those who don’t. Spell out what’s okay to say in mixed company and what’s not.

That’s how I’d do it when developing new platonic friends in social settings, to include someone you like as perhaps more than just a friend. It can be trickier if you’re, say, meeting someone from an online dating site. It’s not always feasible to go super-slow in that situation; people want to know “where the relationship is going.” My formula is this: I go on two dates. I do not tell my date about being a sex worker – and I don’t have sex with him/her. I just have two fun, getting-to-know-you dates. On the third date, I disclose that I’m a pro domme. And I do not have sex with them that night, either. I make them go away and think about it. If they come back for a fourth date? Okay, now I’m comfortable proceeding towards sex in whatever fashion we choose.

I do it that way because unfortunately, a lot of potential partners will back off after that third date. I wish that wasn’t true, but it is. I find it easier on my heart if matters haven’t gone too far. So I’m not saying that’s exactly how you should do it, but that’s the model I have to offer.

Finding open-minded partners and friends is one of those issues that reminds me, “If being a sex worker was easy, everyone would do it.” Pursuing a career in sex work is not a consequence-free choice. Naturally, nothing in life really is – but one sees the effects of this choice rather sharply. However, I know many sex workers who are happily-partnered and have full social lives – including me – so it is absolutely achievable. I wish you very good luck in building a circle of people who love you and support you!

Thanks again to Mistress Matisse for sharing her expertise!

Please send your questions to Dr. NerdLove at his website (; or to his email,