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 (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: This isn’t so much a romantic issue as it is a dealing with a jerk issue.

My sister befriended this guy that she talks to almost nonstop. They call each other every day, and talk for several hours at a time and from a distance it seems like they have a great relationship. However, when she starts talking to me about this guy in detail I get worried.

Based on what I’ve heard he has jealousy issues, holds no respect for my sister, and he doesn’t seem to hold the word no in his personal vocabulary. Just today they got into an argument because this dude kept trying to pressure my 18 year old sister into agreeing to let him impregnate her and she wouldn’t stand for it. His reasoning was that he wanted her pregnant so that other dudes wouldn’t look at her. The other day they got into a fight because he wanted her to give him anal sex and she blatantly refused. When she tried to flip the script on him and asked “How would you like it if I shoved my finger up your ass when you didn’t want me to?” He responded, “It’s different for you because you’re a girl.”

In addition to that, whenever HE decides their arguments are finished he’ll merely agree to whatever she says in an effort to shut her up, not because he genuinely believes and respects her opinion. He’s also prone to making false promises for changed behavior but he never follows through. This is deeply troubling behavior for me to witness. If it were me, I would dump him like a sack of bricks, but it’s not me it’s my sister and she still wants to maintain contact with this guy. How can she better navigate their relationship without feeling like she’s walking on landmines all the time?

Sincerely,

Worried and Frustrated

DEAR WORRIED AND FRUSTRATED: These are the kinds of letters I hate getting WaF, because there’s on reasonable way to grab a stranger by the scruff of the neck and shake them until the stupid falls out. Because, um, HOLY HOPPING SHEEP S

T this isn’t a man, this is horde of red flags in a trench coat. This guy is waving more red flags than a military parade in Tiananmen Square and the best thing your sister can do is dump this guy so hard his grandparents get divorced retroactively. She should be NOPE-ing out of there so fast she leaves a human-shaped cloud behind as she hopes the Nope Train to F

k This S

tville.

You know this. I know this. The problem is that your sister doesn’t seem to get this and short of strapping her to a chair and giving her the full Ludovico Technique, you can’t force her to see it. And since your sister is a grown-ass woman and you’re not her legal guardian, you can’t exactly force her away from him.

Not that this would actually work, mind you. There’s no narrative as compelling to young, naive lovers as “nobody understands him the way I do!” Once they gets the feeling that everyone’s against them and their love, it quickly becomes a “you and me against the world” scenario and I can tell you from experience: that’s more likely to make them double down as it is to make them see sense and break up.

Which makes your handling this tricky. You want what’s best for your sister, but you also don’t want to give this your blessing or your approval just because she’s determined to make her own mistakes.  But just pushing her about how awful this guy is can be a great way to push her into his arms and away from you. As much as I hate to fall back to cliches and song lyrics, when people’re in love with someone (or near as dammit), they can do no wrong and like as not, they will turn their back on someone who puts ’em down. As much as we all wish we could, we can’t force someone to see how much of a s

tbag they’re dating.

But you can lead them into seeing it. Sometimes.

The trick is that it they have to feel like they’re the one who came to that conclusion. There’s no argument more powerful or persuasive than the ones that people come up with themselves. You just have to guide them to it.

So the key is that you need to talk with your sister. You can start this by expressing concern… it sounds like they’re really fighting a lot and the things he’s asking for are incredibly unreasonable. Why does she think he keeps demanding things like this from her? Is it really her responsibility to control other people’s thoughts or reactions? Isn’t it frustrating that he never seems to take her “no” as a “no” instead of the start of a negotiation? Is she ok with all of these demands he’s making on her? Is she comfortable with the way he reacts when she turns him down? She knows that it’s not cool for him to keep pushing after she’s said “no” to something, right?

The odds are good that she’ll come back with a litany of very common responses. “It’s not that bad.” “He doesn’t mean it that way.” “It’s not like he’s serious.” The key here is that you don’t argue with her. You aren’t trying to contradict her sense of reality; that’s more likely to make her double down on her claims that she’s fine, it’s fine, everything’s fine, it’s fine. Instead, you express concern: “Well, it’s just that the last few times you’ve been talking, you’ve been arguing.” “I just worry because it seems like when you’re talking to him, you turn into a different person; it’s like you’re tiptoeing on eggshells around him.”  Rather than asking her to agree with your facts, ask her to agree that your worries aren’t unfounded: “OK, but looking at it from my end, we can agree that it’s reasonable that I might see it that way, right?” You aren’t challenging her facts, you’re just asking her to agree that you’re both reasonable, rational people and that as a reasonable, rational person, your interpretation of things isn’t out of line.

Then you want to reassure her that you’re just worried about her and for her and that you care. Remind her that she shouldn’t let him push her into something she doesn’t want to do and that you always have her back. Emphasize that you two are on the same team and that you are always going to be there to listen and provide support if she needs to talk about things or is feeling weird about stuff.

And then you just make sure that you keep the lines of communication open. She may not necessarily be receptive to this immediately, but by keeping things non-confrontational and supportive,  you help encourage her to come to you when she does start feeling hinky about this guy.

You’re not likely to change her mind overnight, and you shouldn’t expect to. This is more about planting a seed that will hopefully grow into awareness… hopefully sooner rather than later.

Now the thing I would suggest you do be firm about is that she get on some form of semi-permanent birth control… something that he can’t undo or sabotage. Condoms “break”, birth control pills don’t always work and you can be talked into not taking them. An IUD or a hormonal implant (or even Depo-Provera) are all things that he can’t f

k with. Offer to take her to the doctor or Planned Parenthood yourself. Offer to pay for it, if that makes the difference. Even if you have to frame it as “this way you can’t have any accidents”, it’s really important that she not be in a position to “accidentally” get pregnant with him. A lot of abusers will use pregnancy to force their partners into compliance and denying him this chance makes it that much easier for your sister to get the cinnamon toast F

k away from him. And even if he’s not an abuser, just an asshole… the last thing she needs is to be scrambling her DNA with this s

theel.

You’re a good sister, and hopefully you can get your little sister away from this dude with the quickness. But keep in mind: what she needs more than anything else is your support, not your judgement. She won’t leave him before she’s good and ready, and knowing that you’re there willing to provide the love and support she’ll need can be a huge motivating factor.

Good luck. And write back to let us know how it’s going.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I’ve been listening and reading your works for a while now, and I have found your insights and advice really helpful —and your obvert feminism and repudiation of pseudoscience wonderfully refreshing, considering what the standards of the industry sometimes seem to be.

I am a 27 year-old straight male that, one year after a friendly break-up that I’ve spent working on self-improvement, feels ready to get back on the dating wagon.

Some weeks ago I met a girl at work whom I found instantly attractive. I got her number and, after another random meeting at work, started messaging her the next two weeks, during a holiday trip she took. What started as simply making sure that my interest was noticed (so that we could maybe meet after her holidays) turned quickly into daily conversations, and soon after into hardcore flirting by both of us.

She proposed to meet the day after she was back, and ended up spending about 10 hours together, from the early afternoon until after midnight. Everything felt natural and clicked, the sexual tension was palpable, and before the date was over we were making out passionately. All in all a wonderful experience.

Thing is: a few days later we met again, and this time she suggested bringing some friends to the meeting. The night was fun and all, but I didn’t feel there was an appropriate time to make out again: no intimate time, no time just the both of us; still, the chemistry was there, so I didn’t make a great deal of it.

Fast forward to a few days ago, when we met alone right before she went again on a trip, and had the conversation I feel really confused and want to ask you about.

She wanted to talk about how she felt about us, and told me that while on the one hand she felt attracted to me and really enjoyed our conversations, and thought we clicked together, on the other she wasn’t sure about wanting to pursue a physical relationship at the moment. She added that there had been times in her life when she felt pressured by the expectations of others to become physical or sexual with other men even when she wasn’t too sure about it, and didn’t want to experience that pressure again. She also said that she was seeing other people, and really didn’t contemplate the possibility of an exclusive relationship for the time being. She enjoyed everything that had happened so far, and didn’t find any fault with me or my doing.

Much of this didn’t bother me: I don’t know that I want anything serious yet, I’m seeing other people too, and, although I’m REALLY attracted to her (sexually and as a person, and I made sure to state this clearly), I’m nowhere close to infatuation.

The question is: should I assume that she’s not really sexually interested in me (her relatively convoluted way of saying that being simply a stylistic choice) and move on? That being the case, how does that make sense after such a (and I really, really don’t think I’m misreading this) passionate and wonderful date, preceded by unmistakable flirtation and followed by what seems to be a genuine interest to see me again and maintain some form of an active relationship (albeit perhaps a non-sexual one)?

The entire story spans only a few weeks, and it ending without getting any further wouldn’t be tragic, but I’m intrigued by what appears to me as an erratic behaviour or inscrutable expectations, and perhaps there is a transcendental truth I’m not seeing to be learnt from this experience.

Not Sure I Understand People

DEAR NOT SURE I UNDERSTAND PEOPLE: I’m gonna help you out here, NSIUP: the transcendental truth to be found here is… literally what she told you. She’s not ready or interested in a physical relationship. More specifically: she’s not ready or interested in pursuing one with you.

A lot of times, after having been on a couple of dates — some times even just one date — people who just aren’t feeling it will do the courteous thing and tell you. And since they don’t want to be harsh or make you feel bad about it, they’ll often add a softener, something that’s meant to take the sting out of it. And since rejection always feels personal — and some dudes really react badly to being rejected — they’ll phrase it in a way that makes it less of a rejection and more of an obstacle that just can’t be overcome. This is why folks will say “it’s not you, it’s me” or  “I’m just not ready to date.” It’s a shame, if circumstances were different then you two would have a chance but they aren’t, so you don’t. Oh well, what can you do, the stars are aligned against us, nothing to be done about it. Occasionally they’ll even add a “right now” to this because, well, it’s not like they’re going to be single forever.

The problem is that while people will do this as a kindness (or occasionally as a way of not getting murked), the people hearing it don’t quite understand what’s actually being said. That’s why when someone says something along the lines of “I’m just not ready to/ interested in/ able to have a relationship”, you have to silently append the unspoken “…with you” to the end of it.  Otherwise you run the risk of giving yourself false hope (or in some cases, ignoring the screamingly obvious) and holding onto the “for now” instead.

Once you start recognizing this, then it’s easier to start working out just what happened.

Let’s look at what happened with you and your friend, NSIUP. You had a lot of chemistry over text, when you met up you had an amazing date that ended with crazy make-outs. All well and good. But the second time you got together, she invited some friends to come too. That in and of itself is… not a warning or red flag, necessarily, but it’s definitely an indication that she wants to ensure that sex or any physical tomfoolery was on the table. That’s something that folks will do when, say, they suspect that their platonic “friend” just invited them on Schrödinger’s Date. So by this point, your friend was sending up a flag of some sort.

The conversation you had afterwards, about how she didn’t want to pursue a physical relationship with you and how sometimes she felt pressured into getting physical when she didn’t want to gives further clarity to her mindset here. This, for example, tells us that the odds are good that her friends were as much chaperones as they were invited to share in cool goings-on.

Now, the interesting part is that she mentions that she’s also seeing other folks. While this could be taken as “so don’t be surprised if you see my relationship status change”, it could also be an indicator of just why she’s telling you this.

So keeping in mind that I’m not a mind reader and the only person who really knows what this all means is her, here’s my best guess at what went down.

You all had a great date… but somewhere along the line she either started feeling weird about things or she started having questions about where this was going. Things may have moved faster than she was necessarily ready for. She may have caught a vibe that you were more into her, and had more expectations, than she was into you. Something you may have said or done may have given her the impression that you wanted more from her than she was ready to (or able to) give. Or that the make-outs on the first date were nice, she wasn’t quite feeling it as much, and wanted to make sure that there wasn’t any awkward “no, we’re not gonna this time” on the second get together.

And then she had the “It’s not you, it’s me” conversation with you and here we all are.

One thing I want to point out: as harsh as this may sound, she’s actually paying you a compliment by having this conversation with you. She was making a point of doing you the courtesy of turning you down in person and respecting your time by being fairly upfront about things. Those are all generally good signs. A lot of folks would just ghost on you or pull the fade.

But over all: you were feeling it. She wasn’t. You two may not have been right for one another, you may have been at incompatible places in life or there may have been some crossed wires. But at the end of the day, both people have to want to turn the key and she just didn’t.

Unfortunately, the best thing you can do is take what you’ve learned here and apply it to your next date.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com