DEAR DR. NERDLOVE: I’m a very confused and sexually frustrated 22 year old (non-religious) virgin male. Being a virgin this long has had a strange effect on me, simultaneously making me feel both more worthless (obviously) and more special/rare. I’m not at all the “hot” or machismo type and have never felt any pressure to be. I get by with women by being “cute,” sweet” and “adorable.” Therefore in all the times I’ve played out in my head the “Baby, I have something to tell you… I’m still a virgin” conversation, I’ve never imagined it going poorly. I think most girls I’m attracted to would jump at the chance to take my virginity. Ironically, it’s people like my parents who I hope think that I’ve had sex. I can accept a pity f

k, but not conservative Christian parents’ approval. I say all this, Doc, because I’m not sure if the issue I’m about to tell you about really has more to do with my own virginity and my complicated, slightly atypical thoughts around it, or the virginity of another individual.

Here’s the catch that may make me an asshole: it’s not only my virginity I fret about, but also that of the girl I’m currently into. Long story short, I’ve been sexting this girl online for over a year. She’s quickly become one of my best friends and we’ve both developed feelings for each other. We say we love each other and belong to each other. It’s a long distance thing, so we’ve never met in person or put an official “dating” label on our relationship. Last week she lost her virginity. When she told me I was shocked at how nauseous and disappointed I felt. Regardless of how attractive she is, when I think of her body I now struggle to think of anything other than another guy pumping his semen deep inside her, and it makes physically ill. So one of my questions, Doc, is essentially: How do I get over the irrational, sickening idea of “sloppy seconds”? (To be fair, I think even if I were female I wouldn’t like the thought of my man being or ever having been inside another woman.)

I think I’ve read every bit of virginity advice you or a guest columnist has ever written, and I know, rationally, that’s it’s just a stupid social construct. Aside from STD’s I’m pretty sure it’s not scientific to believe in the lingering DNA (read as: semen) of previous lovers, right? However, irrationally, I can’t shake my feeling of disgust. This strong adverse reaction has taken me completely by surprise. After all, I’ve had crushes on non-virgins in the past. Yet in this one particular case I can’t help but be disappointed in an admittedly kinky “I wanted to deflower her” way, but also, I really want to stress, a hopeless romantic “I wanted us to ‘give ourselves to each other’ in a way that neither of us ever had before to another person” way.

Like I mentioned at the start of my post, I’m not sure if this issue really has more to do with her or myself. All week I’ve been having to ask myself tough questions: Why do I care? Am I an asshole for caring? Why has a girl’s virginity status never bothered me so much before? Will I ever (hopefully) go back to my indifference? If not, how will I live a normal adult life? And why the hell am I still a virgin? How much does my virginity mean to me? Etc.

Is there anything you think might help me get over this major turn off? Or perhaps can you pen the definitive, scientifically supported “Virginity Is Not A Big Deal!!” article to end all “Virginity Is Not A Big Deal!!” articles? The older I get the bigger this issues becomes, and the more it seems to entrap me in my own head, mentally separating me from normally functioning adults.

Thanks for your help,

Irrationally Obsessed With Virginity

DEAR IRRATIONALLY OBSESSED WITH VIRGINITY: So, fair warning, IOVW, this is going to be rough. Before we get started, I want you to realize something: I don’t think that you’re a bad person or that you’re an asshole. This s

t is clearly bothering you – a good thing! – and you’re reaching out to fix it. So while this is going to sound harsh, the problem isn’t you so much as what you’ve learned. Sometimes ya gotta take the Chair Leg of Truth to some deeply held beliefs. So brace yourself, ok?

Your problem isn’t with virginity, IOWV, it’s with sexuality. You’ve gotten your head wrapped up in all sorts of bulls

t ideas surrounding sex, virginity and masculinity, and if you want to improve, then you’re going to have to start untangling that mass of complexes that you have floating around in your brain.

Let’s start by pointing out the obvious: you’ve got a doozy of a Madonna/Whore dichotomy going on that’s getting tied up with some shame about being a virgin alongside fairly serious entitlement issues and it’s coloring everything. You have this long-distance pen-pal that you’ve been sexting with and you’re totally cool with the idea of her f

king you…. but if anyone else puts their hands on her and suddenly she’s dirty and disgusting and dripping with sloppy seconds. The problem isn’t that she’s had sex, it’s that she’s had sex with someone else. Somebody else has put their hands on somebody you considered your “property” and now it’s ruined. You’ve had plenty of fantasies of banging other women and that only serves to enhance you – you become a “real man” at the end. Even a pity f

k is ok because hey, “any sex is good sex”, right?

(Spoiler alert: no. No it is not. Trust me on this – there will be plenty of times when even sex you think you wanted is not good…)

Now before we unpack this some more, I want to point out that yes, I totally get the jealousy thing. You’re worried that you’ve lost out on something by the fact that she’s had actual sex with someone who is not you. It’s totally understandable – everybody deals with it and the best thing you can do is let yourself feel it. But here’s the thing I want you to think about: how unfair this is to your friend. She’s opening up to you because she trusts you and because of the emotional (and, presumably, sexual) intimacy you have together. After all, she’s your best friend – why wouldn’t she want to let you in on this part of her life? And here you are getting angry and disgusted at her because of things that are entirely your baggage. This doesn’t affect you in the slightest. She’s exactly the same person she was before she had sex; the only difference is that she’s had a new experience with someone else.

And that’s where things start getting f

ked up. You say you wanted that “Share something special with each other” moment with her, but it’s less about the two of you than it is about you; you wanted to be the one to take her virginity. I mean, you’re totally cool with pity f

ks or these random fantasy girls jumping at the chance to make you a man because hey, it’s you. The fact that you wouldn’t be a virgin with anyone else wouldn’t degrade or lessen your relationship with them, would it?

I realize this is sounding kind of harsh, and I want you to realize I’m bringing all of this up not because I think that you’re a bad person but because I want you to think about these things. You have a whole lot of assumptions and beliefs surrounding sex and sexuality that you’ve let go unchallenged without realizing how f

ked up they are – and it’s only by confronting them that you can get past them. For example: let’s break down the whole “sloppy seconds” issue you’re having right now with a thought exercise. I’m going to make the (admittedly, relatively safe, statistically speaking) assumption that you watch porn and have gotten aroused by it; perhaps you jerked off while watching it, or used it to fuel a fantasy for later use. You’re watching someone else pound away at this person you’re interested in f

king… do you have the same sloppy seconds revulsion, or are you able to ignore the dude and just insert yourself in his place in your fantasy?

(There’s also the possibility of getting aroused specifically because someone else is f

king someone you want, but that’s a different subject all together…)

If you’re like most men, heterosexual or homosexual, that other person doesn’t phase you even though they’re f

king someone you want to f

k. They don’t interfere with the fantasy because you’re not caught up in being the first or only person to have sex with the person you’re thinking about. You just want to bang ’em.

Now, with your friend, you’ve fetishized taking her virginity. Why? Because that’ll make you special. It’ll make you different from any other guy she dates. Except… how, exactly? Why does being the first person to stick your penis into her make you more special than being the person she most wants to see at the end of the day? Why is your boner being the first she sees more important than being the person she most wants to share her hopes and dreams with?

I’ll tell you why:

First, because you don’t believe you can stand out – or compete, for that matter – in any other way. If you’re somebody’s first, they have no basis for comparison; you are by definition the best f

k they’ve ever had with the biggest, most magical dick. It’s bulls

t of course; just because somebody is another person’s first doesn’t mean that it’s the best or even all that good. In fact, the sex they have with themselves may well be far better than the first time they have sex with someone else. But hey, as long as you can say “yup, I was first”, it gives you an overinflated sense of being “special” for no real reason.

(If you ever want to see this mentality in action, watch Chasing Amy. Ben Affleck’s character Holden has no issues with Joey Lauren Adams’ Alyssa having had sex with other women… but as soon as he finds out that she’s not only been with men but she’s had kinky, experimental sex with dudes too he freaks the f

k out. Why? He was cool with the women because hey, he’s Going Where No Man Has Gone Before and that makes him Special with a capital S. But once he learns the truth, he doesn’t feel like he can measure up with the fact that she’s more experienced than he is and the fact that she loves him doesn’t make him special enough.)

This gets tied up in your own issues with being a virgin. You don’t feel like you’re a man – as you put it, you get by on being “cute” and “sweet”, diminutives that carry the connotation of childishness – and so her having had sex means that you can’t prove that you’re “good enough” to deflower a virgin. Now you have to “compete” with all of her other lovers. Never mind the fact that we don’t base who we date or sleep with on how they stack up to everyone else we’ve ever been with.

And second, because it imparts a sense of ownership. It’s part of the f

ked up ideas that our sex-negative culture teaches us about sex and virginity: first one to stick it in someone owns them for life. You see this in the Abstinence Only educational movement and in the ha-ha-no-but-seriously anxiety “jokes” about virgins imprinting on their first partner like a baby gosling. By being their first, you’ve planted a flag on them like Columbus in the New World and everybody else who comes later has to acknowledge your supremacy… even if the only reason they slept with you in the first place was simply to get the whole “first time” thing over.

That’s part of the issue you’re having with the “sloppy seconds” and how it’s ruined her for you: someone else “owns” her now.

Except they don’t. They never did. Neither did you. People don’t own other people.

(Also: semen doesn’t even stay in her that long; gravity gets rid of most of it, the vaginal tissue’s capability for self-cleaning and basic hygiene gets rid of the rest. The oft-quoted “semen stays in her seven days” is a misunderstanding of how long sperm stays viable, not how long actual seminal fluid stays in a woman’s vaginal canal.)

The thing that makes you special to somebody isn’t about being their first or doing things that they’ve never done with other people, it’s being the person they care about. Being that someone special to your partner means far more than who touched how many peenors or hoo-hahs… and is far more difficult.

Talk to some women, find out how many of them don’t see their first time as “special” or “magical” but “a thing that happened” or something that pales in significance with the times they had sex with someone special later on. And work on decoupling your belief in your own manhood from whether or not you’ve stuck your dick in someone; the sooner you’re able to do that, the sooner you’ll be on the path to true manhood.

Manhood isn’t about sex, it’s about maturity.

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: 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