DEAR DR. NERDLOVE: I (29M) recently started dating a very caring and intelligent guy (25M). We have been together for about three months.

Shortly after we started talking, he told me that he had recently ended a long term relationship. From what I have been told, it seems like this relationship had been heading downhill for quite a while before it actually ended. My boyfriend has been very upfront and transparent about it. His ex is part of his circle of friends, and he would like to remain on friendly terms with him. When he initially brought up this situation, he told me that he spoke with his ex and said that while he’d like to be friends, he would like to take a break from communication to focus on our relationship and allow things between the two of them to cool down. His ex asked him for an exact date when they could resume communication, clearly not understanding that it’s not possible to put an exact timeline on these sorts of things.

Recently, I have seen his ex’s name pop up in his messages. I want to be clear that I haven’t been snooping, I’ve just noticed occasionally while he is showing me something on his phone. Seeing this picks at my worse insecurities. It’s very intimidating to know that he is communicating with someone he had such a long and recent relationship with, and it makes me worry.

Besides this issue, I am really enjoying our relationship – and while it is new, I feel that it is strong. I absolutely trust my boyfriend. He is someone I have known for many years, and I do not believe that any cheating is going on. However, my anxious brain often takes over, and it makes me feel like there is no way that I can compare to his ex. I want to talk to my boyfriend about how this communication makes me feel uncomfortable, but I don’t want to come off as controlling or overbearing. I don’t want him to cut off communication unless that’s what he truly wants to do.

Should I just let it go? Should I bring it up?

Ex n’ Effects 

DEAR EX N’ EFFECTS: You should let it go, EnE. But in the process of letting it go, it’s a good idea to ask yourself just why your boyfriend being in contact with his ex is bothering you.

One of the things I’ve noticed is how often people get hung up on the fact that their partners still have relationships of one sort or another with their exes. More often than not, it tends to stem from a feeling that nobody would want to be in contact with a past lover if they didn’t have ulterior motives. Maybe they’re still hung up on their ex, maybe they’re hoping to get back together… the reasons are various and honestly, fairly irrational. While yes, there are folks who can’t let go of past relationships — I doubt I would get all that witch doctor love spell spam if there weren’t a market for it — the fact is that having a solid post-breakup relationship with an ex is a good sign. Somebody who has a positive relationship with their ex — whether it’s just cordial and respectful or a close friendship — tends to be someone who treats their current partners well and with respect. It’s a reliable indicator of someone with strong emotional intelligence, who was able to stick the dismount on the break-up and hold on to the core of respect and affection that he and his partner had, even when things didn’t work. A lot of times, they also tend to be the ones who were able to hash out whatever issues caused the relationship to end and move to the next stage of their relationship without having those lingering resentments and conflicts hanging around in the background.

Those are all qualities you want to find in a partner.

The ones who never have good relationships with their exes, who never have a good word for anyone they dated or seem to have nothing but a string of “crazy” or “evil” exes? Those are the folks you should be giving the side-eye to. The way they talk about their ex is a fairly reliable indicator of what they’re like in a relationship.

Just as important though is the fact that the length of a relationship isn’t a measure of feelings. Yeah, your boyfriend was in a long-term relationship with this guy… but from the sound of it, the quality of that relationship wasn’t great, and hadn’t been great for quite some time. That’s going to be a bigger influence on how he feels about things now than the fact that he and his ex had been together for X number of years. A ten year relationship is one thing, but if six of those years were lousy, then the odds of his wanting to go back to it are slim at best.

And of course you don’t compare to his ex. That’s kind of the whole point: you’re not his ex. With the exception of certain f

ked up individuals who were rather proud of ranking their friends’ qualities on spreadsheets, people don’t pick who they date by ranking their qualities and picking the person who has the highest overall score. They date the whole person, with all the pros and cons that come with them. One ex may have been the most amazing cook, another might have had sex drive and imagination to make Caligula blush, another might have had a singing voice like a choir of angels… but each of those people were chosen on the strength of them as an individual, not points on a graph. Your boyfriend’s ex may have a whole lot of entries in the pro side of the column… but the con is that he’s not you.

The more you can recognize that and hold onto that, the more you’ll understand that you’re not in a competition, you’re in a relationship. Letting your anxiety create conflict where there isn’t any is just how you borrow trouble from the future.

Your boyfriend’s been pretty upfront and transparent about his break-up with his ex and the relationship they’re likely to have going forward. That’s all this is — the beginning of the next stage of their post-romantic relationship. It’s only going to be a threat to you and your relationship if you let it be one… especially this early on and with no reason to worry.

Take a deep breath and just let this one go. And if you’re feeling a little insecure, ask your boyfriend for a little sweetness and reassurance.

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

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