Ask Dr. Nerdlove by Harris O'Malley

How Can I Learn To Be the Person I Pretend to Be?

DEAR DR. NERDLOVE: I am a phone sex operator, and I make really good money doing it.  I’m also working towards a post-graduate degree.  And, of course, I’m a nerd.  Now the screwed up thing about my situation, well the thing I think that the majority of your readers would have, and I’m taking a big risk here as you might as well, a problem with is that I’m a straight guy who manipulates his voice to sound just like a woman. I use my nerd knowledge and my talent to portray a nerd girl over the phone in a fantasy manner. I’m not into guys at all and that is 100% of my customer base, but I have a knack for the naughty and really detailing what I would like to hear from a woman and it turns out the majority of my customers like to hear that too.  So I do well in what I do but I believe that it is hindering me from finding a girl of my own.  

I have my fun with my coworkers, other PSO’s, and that’s fine, but they are not interested in a relationship.  They have made it clear and being a PSO myself I definitely respect their position.  I would never want a customer of mine to track me down.  I’d be so freaked out if I ever actually met a customer face to face.  I’d be afraid they’d kill me for what I put them through.  I also find that I’m pretty socially awkward to the point where my friends have friends that they will not introduce me to because they don’t want to lose those friends. 

It’s true that I found your site by googling how to hit on girls at comic con, but I have a different definition of where I think hitting on a girl should lead. It’s not about sex for me. as I can get that anytime I want, it’s about building a relationship.

But in order to do that you have to say hi and introduce yourself and be personable and I only seem to be that with my customers, not out in the real world.  Is there a way that My working persona can become my actual persona?  and is there a possibility to find a woman out there who would be interested in dating me knowing what I do for money or should I keep that a secret til the day I die?

Struggling PSO

DEAR STRUGGLING PSO: Congratulations, PSO, you’re officially the most interesting questioner I’ve had in quite a while. I’m not even entirely sure how I’d classify your job. Vocal crossplay?

That being said, you have a very common problem: how to become more confident and less socially awkward. Now, this is somewhat hard to diagnose; you don’t say what it is that you do, but apparently it’s so bad that makes your friends decide that they’re never going to introduce you to people for fear of your offending them so badly that you drive them away. I’m assuming that you don’t do anything so outre as to just whip your dick out and start demanding people watch you masturbate or start getting handsy before they’ve finished saying “Hi, nice to meet you.” Maybe you come across as a full-on creeper. Maybe your sense of what makes for appropriate conversation is night-and-day different from other people’s – after all, when you’re working as, and mostly associating with, sex workers, your day to day conversations are gonna be a little different from everybody else’s.

Ultimately what you need is a LOT of social calibration and self-awareness to help curb the awkwardness. Your friends may be able to help you identify exactly what it is you’re doing that freaks people out; once you can identify your behavior, it takes time and experience to learn how to dial it back and be more comfortable and functional, socially. This will, however, entail, making mistakes and learning from them; failure is how we learn, so you’re going to have to be willing to take the hits, as painful as it will be, and chalk them up to learning experiences. You’ll get rejected a lot on your progress to curbing your social awkwardness and you will need to find the strength to not let it drag you down into helpless despair.

Now as to making your working persona your real persona… well, there’s a reason why we have the phrase “fake it until you make it”. It may well help to see yourself as playing a role, just as you do when you’re dealing with your clients over the phone; if you’re able to inhabit the role so well that you’re able to convince strangers that you’re a nerdy young woman instead of a guy, then you should try adopting the role of a smooth, charismatic man. Just don’t make the mistake of assuming too much insight into women based on your phone-sex work; you may be used to playing a girl, but that girl is a male fantasy. She’s designed to be appealing to guys who want to jerk off, not to be a fully-realized person with her own experiences and personality.

As for the job? Well, you have a couple of options. You can be up front about it, or you can hide it until either you feel more secure in sharing it… which may mean taking it to your grave. If you do decide to be upfront, you shouldn’t be apologetic about it; you’re explaining that you’re a sex-worker, not that you have an untreatable disease that randomly makes you fling cat s

t at passers-by. You are providing a fantasy for people, and you’re comfortable enough with your sexuality that you have no problem with the fact that your clientele are men. You want to present it as a feature, not a bug.

If you do decide to hide it… well, most secrets tend to come out regardless of your preferences. Some women are going to feel as though you were lying to them by not telling them. Others will feel insulted that you felt as though you couldn’t trust them and still others will feel that you betrayed them by hiding this – especially if they’re the sort of person who has negative views about sex-work.

There isn’t going to be one universal answer because individuals are going to feel differently about it, so you’re going to just have to approach this on a case by case basis. Though if you want to maximize your chances of your future partners not having a problem with your being a phone sex operator, I suggest you focus on seeking out people who’re sex-positive and support sex-workers’ rights.

By the by: there are plenty of sex workers, male and female, who have relationships with partners who know exactly what they do and are ok with it. It can take time and effort to find someone that accepting, but it’s always worth it. Take some time to Google around; there are resources out there for helping negotiate the tricky paths of maintaining a relationship with someone in the sex industry.

Good luck.

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