DEAR DR. NERDLOVE: I grew up in a religious household, one that strongly believed in the idea of no sex before marriage. I had chosen to remain a virgin until marriage, but wound up losing it anyway. This upset me pretty badly, made worse when my family found out. I’ve since had more experience (always feeling guilty), had in toxic relationships that I stayed in only to validate the activity. It’s been a long struggle, but I’ve become comfortable with myself and who I am and want to be, especially sexually.

I am now dating someone in my own faith and assumed I would wind up returning to my original choice to wait, especially since he was a virgin. As you may guess, this did not happen, but I find that this time, I’m actually comfortable with the result and enjoying myself and him in a way I never did before. I’m still having one problem, though. He is aware of my sexual history before him and, while he’s never said or even implied anything derogatory, I still feel embarrassed and ashamed at anything that hints at my past. I feel uncomfortable with the fact that I know what I’m doing and with telling him what I like. Half the time, I find myself laughing uncontrollably while I try to spit the words out, but mostly I just want to curl in on myself. I’m almost there, but can you help me cross that final barrier to being a confident sexual being?

– No Longer Waiting

DEAR NO LONGER WAITING: Oh man, there’s so much in this, NLW that I don’t really know where to start.

Actually, I take that back.

Your letter nicely illustrates one of the biggest injuries that our sex-negative culture inflicts on people – women especially. Now I’ll be the first to say that people are welcome to take sex at their own pace and wait until they’re ready. That being said, I think that waiting until marriage isn’t a good idea; sexual compatibility is an incredibly important part of a relationship and one’s wedding night is a very bad time to find out that the two of you have entirely different ideas about sex. I think that this attitude robs people of the opportunity to explore their own sexuality and get to know just what they want, how often they want it, how they need to get off and what they will or won’t consider when it comes to indulging a partner’s fantasies.

Just as importantly however, is that it perpetuates the commodity model of sex – that a woman’s worth is based on the amount of sex she doesn’t have – and perpetuates the Madonna/Whore view of women. And that’s where the damage really starts to sink in. It’s bad enough when guys internalize the idea that women who’ve had lots of sex have something fundamentally wrong with them, but the damage that it does to women, not just to their psyches but their lives.

Bad enough that you lost your virginity in a way that — from the sounds of it – was not the way that you wanted. Even more so that your family got involved – evidently blaming you, because of course women have to police men’s sexuality (he said, his voice dripping with sarcasm and trying not to vomit). But it was this line in your letter NLW really leapt out at me:  

“I’ve since had more experience (always feeling guilty), had in toxic relationships that I stayed in only to validate the activity.”

That, unfortunately, is an incredibly common story, especially among women I’ve known who’ve come from backgrounds similar to yours. One of the side-effects of the sex-negative culture in America – the wackos who insist that women should be virgins until marriage and have no sexual autonomy – is that it promotes the idea that “if he puts his d

k in you, he owns you for life.” There’s an implied sense of obligation to stay now because – as Elizabeth Smart articulated brilliantly – you’ve been taught that you’re worthless and nobody is going to want you now. I’ve got very good friends who, like you, stayed in toxic, even abusive relationships because they were taught that sex was dirty and shameful unless it gets the holy stamp of Church and State approval; leaving the relationship would only mean that they’d done something wrong in the eyes of God and man.

So, yeah. I’ve kinda got a beef with the people who teach sexual shame and trade on ignorance, fear and negativity, especially in the name of a caring and loving god. The damage they do is farther reaching than I think anyone realizes.

Case in point: you’ve had a long and difficult struggle with coming to terms with your sexuality and being willing to take ownership of your life… and frankly you should be applauded. This is an incredible testimony to your strength and perseverance and your determination to push past the bulls

t that people tried to instill in you. It’s awesome that you’ve come to a place where you can actually enjoy your sexuality like you should and be comfortable with yourself. You should be proud of yourself and your progress… and most importantly, you should not be embarrassed by your past.

Those last niggling doubts and feelings of shame are the last little tendrils of the utter crap you were taught, holding on for dear life around your brain, and it can be hard to extract them. In fact, your brain will actually fight against it at times, even though you know intellectually that it’s wrong. It is very difficult to break old patterns and habits, even when you understand that they’re bad for you. You may notice that these feelings crop up hardest when you feel like you’re about to make a breakthrough – just when you’re starting to truly feel like you’ve come into your own, suddenly there’s that little asshole voice in the back of your head that whispers “Don’t forget, you’re slut and nobody can possibly love you. If he knew what you were REALLY like he’d be disgusted.”

This is what’s known as an “extinction burst”. Because you’re getting close to overcoming this old programming, there’s a part of your brain – the part that absorbed all of these lessons – that says “wait, if I don’t do something, this is going to go away” and suddenly it floods you with feelings of shame and remorse. It’s the emotional equivalent of someone on a diet who suddenly goes on a binge of crappy food. The difference is that while breaking the diet is based on a physical reward system – your body’s used to the high it gets from carbs and sugar and fat – the other is psychological. You’ve been brought up to believe that questioning your beliefs were wrong and that any deviation from these strict teachings means you’re a horrible person who deserves to be punished. Now that you’re starting to step away from those beliefs – you have your faith, but you no longer believe in their dictates regarding sex – that little part that’s supposed to keep you from breaking away is firing up and trying to bring you back into the fold.

It’s also complete bulls

t.

The fact that you have a sexual past is inherently neutral. You’re not a bad person because you’ve had sex; the only bad parts were the ways that you were hurt in the process. The fact that you know what you like sexually and want to to tell him? This is unquestionably a good thing. In fact, this is an unbelievably desirable asset in a sex partner, especially when the other is relatively inexperienced. Let’s look at it from another angle: your boyfriend has somebody confident, caring and patient, who wants to teach him how to please a woman instead of letting him fumble his way, learning all the wrong lessons and getting frustrated in the process. Who wouldn’t want that in a partner, especially their first? 

This is what your jerk-brain is trying to deny you. It’s trying to take a strength – your hard-won experience – and turn it into a weakness. And you shouldn’t let it.

By all accounts, it seems like your boyfriend’s a cool person who’s not judging you by your number. You care for him and trust him… so take “yes” for an answer when he’s giving you every indication that he’s not intimidated by your past. And if he – or any guy you may date in the future – has a problem with the fact that you’ve had sex before… well, that’s their problem to overcome, not yours. A guy who can’t handle the fact that his girlfriend or wife has a sexual past can hand back his man-card; he’s not a man, he’s a boy and he’s got some growing up to do.

I’m the biggest believer in affirmations, but whenever you have that voice from you jerk-brain piping up,  remind yourself that you’re strong, that you’re desirable and that you deserve the sex you want and anyone who says otherwise is cordially invited to go f

k themselves. Your past – as painful as it was – has lead you to who you are today, and from the sounds of it, that’s a pretty amazing place. And that past includes the people you’ve slept with. It’s molded you. It’s shaped you, it’s tempered you and tested you and you’ve come out stronger and better for it.

Nobody can take that from you if you don’t let them.

Enjoy the sex you’re having with your boyfriend. Revel in it. Teach him how to f

k you in all the ways you want to be f

ked. Take pride in where you are and what it’s taken to get you there and reap the rewards of being a sexually confident woman. There’s nothing to be ashamed of; there are only small-minded chucklef

ks who’ve tried to convince you otherwise. And you’re stronger than they are.

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: Long time reader, first time (cis, female) writer. Recently my best friend in the whole world came out as a trans woman. I’ve known her for over 10 years and we spend most of our free time together. We’re your typical geek cloister: we live movies and comics and taking them way too seriously and having college-thesis level discussions on how media intersects with society, etc. I’m sure you know the type! I was so excited that she was finally leaning about herself and learning more about her true identity. I’m trying to be 110% supportive of her transition, but here’s the problem:

Now that’s she’s becoming a woman, I feel like I’m losing my BFF. Because the woman she’s becoming is this preening, pretty, make-up obsessed “girly girl” that I just can’t stand. Now, I don’t mean to s

t on any other fellow females who are into that scene – but its NOT ME. I’m NOT a girly-girl… in fact I’m pretty staunchly one of those women who is very outspoken by how “traditional femininity” is toxic and harmful. I hate how women are expected to adhere to certain beauty standards and are expected to wear make-up and do their hair to be taken seriously in almost any social situation – including job opportunities. I’m not against make up and pretty clothes on principal – but I do have issues when you’re not taken seriously as a woman if you’re not “made up” or skinny enough or adhering to a certain beauty standard.

But it seems with my friend – let’s call her K – is transitioning that’s what she’s obsessing over. She’s made changes to her appearance for her “every day” look that makes her feel more comfortable (she wears earrings, got a new hairstyle, paints her nails, etc) but whenever we want to go ANYWHERE where other people may be, she wants to be “dressed up” – and I mean to the nines. She spends about 2-3 hours doing her hair, make up, jewelry, fully co-ordinated outfit…even if we’re just wanting to grab a quick bite to eat or go catch a movie. She says she doesn’t feel “right” unless the outside world is treating her/recognizing her a woman so she’s become increasingly obsessed with clothes, shopping, make up, voice-training – basically all the trappings of “femininity” that makes me want to throw up in my mouth a little. And while I can understand how she wants to “feel like a real woman” and be treated a certain way in public – my issue is that it feels like she’s succumbing to every little thing about what women are “expected” to look like, sound like, and behave like that I find so disturbing.

If she doesn’t feel like a “real” woman unless she meets these mental standards of what femininity is in her mind – in my opinion she’s feeding straight into the toxic subculture I hate so much. And again, I don’t have a problem with girly-girls if that’s what they truly enjoy (women can look however they want to – as long as it’s what THEY want, and not because they are bending to some societal pressure imho), but what’s terrifying me is that I feel like I’m losing my best friend. I want to go back to being best friends who talk all day about Marvel and politics and space…. not bras, dresses, and make-up.

I know there’s a lot of stages to transitioning, and I’ve tried to talk to K a bit about this and she basically just says I’m being intolerant and that it’s not her fault that society treats women like they do (which is true, but I think by succumbing to their demands you’re feeding into it) and that she won’t ever feel like a real woman as long as other people see her a woman. I’ve tried to explain to K that she’s a woman regardless if she’s just in a t-shirt and jeans or all decked out for a night on the town.

Help? Am I being unreasonable by being so dodgy and uncomfortable about her new obsession over being a “pretty girl” or is she just becoming a new person that I may have to let go? The thought of losing my best friend is devastating, but I kind of feel like I already have.

Not A Girly Girl

DEAR NOT A GIRLY GIRL: OK, I’m going to qualify this with a disclaimer: I’m a cis straight man, so this is all coming strictly from my limited perspective. I will probably miss some angles here that will be glaringly obvious to someone who’s trans, genderfluid or non-binary. So, everyone please take what I have to say with all appropriate amounts of salt and my sincere apologies if I step wrong.

That being said: welcome to a complicated intersection of gender performance, trans acceptance, passing, feminism, beauty standards and a whole host of other issues. This is one giant-ass knot that’s very nature is going to defy any easy unpicking. But let’s start with the most obvious. Your friend is transitioning and – quite understandably – is wanting to be accepted as her gender identity by the world around her. As I’m sure you already know, there’s a lot of pressure for trans men and women to pass or measure up to an “acceptable” level of masculinity or femininity. There are plenty of people who will take any example of a trans woman not being perfectly femme as proof that she’s not “really” a woman. This is a world where people still feel empowered to talk about “chicks with d

ks” or making jokes about dudes throwing on dresses and calling themselves women in order to win the Olympics or sneak into bathrooms. That alone is going to put a lot of pressure on her to “be a woman” in a specific manner; it’s easier to “pass” and be accepted as a woman if you present a more traditionally feminine exterior.

On top of that, there’s the fact that while you grew up with the cultural ideas of “what is a woman”, K… didn’t. Not the same way you did or the way that I grew up with the cultural ideas of “what is a man”. For us, our gender expression is second nature, even if our personal values may or may not conflict with the culture around us. Your friend K is having to learn and adapt to these. Yeah, she’s always been a woman, but she grew up being taught how to be a man. She’s correcting the mistake now but it’s still going to be closer to learning a second language instead of using the one you grew up with. You’re fluent in “being a woman”; she’s still learning. There’s going to be a lot of adjustment there and it may be easier to veer to the very traditionally feminine until she feels more fluent.

(Incidentally, if you want to see a great example of this from the other direction, writer, editor and podcaster-par-excellence Jay Edidin has written a fascinating series for MEL about having to learning how to perform masculinity as he transitions. Check it out.)

She could also be experimenting with just who she is and starting off at one extreme for a while and may decide she doesn’t want to be as girly later on down the line as she gets more settled into her life. She may decide that she isn’t as concerned being femme and could adopt a more androgynous or butch style.

Or she may just be really femme and likes feeling pretty. Gender performance does fall on a spectrum after all. Some people just like coordinating their outfits and making sure their hair and make-up is perfect when they leave the house. For the first time in her life, she’s now in a position to get done up the way she’s always wanted to, so she’s indulging. It may be a permanent thing – the tiger’s finally off the leash – or it could be that it’s new and shiny and for right now it’s where her interest lies. It may well be like someone who’s suddenly gotten into a new TV show or a new diet or some other new part of their life that takes up 90% of their attention for a while.

Is it excessive? Maybe? Is it permanent? Dunno. It’s impossible to say.

For right now, I’d say give her some space and find herself. She may level out, she may veer in the other direction. It may help both of you if you introduce her to some people who are more into her style of femininity. This way, you’re not feeling like you’re getting dragooned into being her guide to a form of femininity you’re not crazy about and she’s got someone she can geek out about makeup and dresses with. That may take the pressure off and she’ll be ready to talk more about comics and politics with you again.

The thing to keep in mind is that this is probably the first time in her life she’s felt entirely her. This is an exciting and scary and possibly overwhelming time for her so she could really use her friends right now… even if you were wishing she wasn’t quite so girly.

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 come to you seeking advice on my issue with casual sex. Currently I’m 27 and I’m starting to notice some issues when it comes to hooking up with girls I’m not romantically involved with. When I was younger (18-23) it was easier for me to dissociate feelings with sex. I would be perfectly okay with no communication or not seeing someone again after a one night stand. Now things aren’t as easy and I find myself becoming emotionally attached to the women I sleep with even though I know they’re not someone I’d be in a relationship with (and the same with them).

A little background info on me… I spent a year in Afghanistan from a deployment with the Army and I came back thinking everything was fine because I didn’t have any traumatic experiences. It turns out I was worse than I thought, I was anti-social and separated myself from friends and family. When I did hang out with people I was kind of empty inside. I believe now I’m passed those feelings but my issues with feelings after sex are worsening.

I recently hooked up with my friend from the army’s sister (Her and I are friends too but through him). It was not only a terrible night of sex because we were both really drunk but I found myself nearly depressed the next day. I felt feelings of rejection and projected a lot of feelings in my head that she never really even hinted at, she’s more of a free spirit so it was completely casual. It’s like I’m torn, I know that we would never date because she lives a ways away and I don’t think we would make a good couple, but I also feel like I should date her and almost feel guilty about the night we had. How do I dissociate these feelings? Why do I feel like we should be dating and also being content with being friends despite the massive contradiction? This isn’t the only time it’s happened, just the most recent.

I appreciate your time!

-Some Strings Attached

DEAR SOME STRINGS ATTACHED: As with many people who write in, I think the problem you’re asking about isn’t the problem you’re having, SSA.

See, I think your problem’s pretty clear: you’re dying for a connection with someone… anyone. I mean, you say it yourself: you spent a lot of time separating yourself from your family and friends. However, you’re also craving connection and emotional intimacy and you’re probably feeling intensely lonely and you’ve got this part of you that’s reaching out for almost anyone who comes within your orbit. You’ve pushed away a lot of the people who you were close to and so now this part of you that’s craving a human connection is trying to build it up with the people you’re hooking up with.

Now keep in mind: Dr. NerdLove is not a real doctor and nothing I say should be taken as anything even vaguely like medical advice. However, the thing that leaps out at me is your social isolation and feeling empty… those tend to be pretty big warning signs and ones that correspond a lot with people dealing with emotional trauma and PTSD. You say you didn’t have any traumatic experiences, but that doesn’t mean your time over there didn’t affect you. Similarly, the fact that you’re not digging trenches in your back yard or having flashbacks doesn’t mean that you’re not having problems; a lot of people coming back have issues reconnecting with family and friends or feeling whole again. And to be quite frank: issues like that doesn’t just go away… especially on it’s own. You don’t talk about whether or not you talked with a therapist after your deployment, but the way you describe things makes me think you didn’t. It sounds to me – and I freely admit I could be wrong – that you tried to white-knuckle your way through things and waited to get better. Maybe you did, maybe you didn’t, but either way it really doesn’t seem like you’re past those issues.

That’s why I think that you’re looking in the wrong direction. I don’t think the problem is that you’re catching feelings from random hook-ups, I think the problem is that you’re having a hard time after an emotionally trying, possibly overwhelming experience. Trying to distance yourself from the people you’re sleeping with is a mistake because not only is that treating a symptom rather than the source, but it’s just reinforcing your isolation and disconnection.

Again: I’m not a doctor, I’m a loudmouth with a blog. However, a doctor or therapist is exactly who I think you should be talking to right now. The fact that you can’t point at any single thing that happened to you doesn’t mean that you on your deployment to cause a problem doesn’t invalidate how you’re feeling. You don’t need to have been in the middle of a giant explosion, crash or ambush to have gone through some s

t and need to talk to somebody. ER nurses, first responders, social workers and other people who don’t go through combat or assault suffer from PTSD, after all. Similarly, asking for help or going to talk to somebody – even if it’s just about a vague sense of unease – isn’t something to be ashamed of, or something that makes you weak or unable to hack it. It makes you human, same as everyone else. And humans need help on occasion. It takes some real strength to admit that sometimes you can’t do it on your own.

The best thing you can do right now is to find a counselor to talk to about your self-isolation and the way you’re responding to sex would be a good start.

Good luck. And write back to let us know how you’re doing.

DEAR DR. NERDLOVE: Long-time listener, first-time caller. I’m having trouble coming up with a positive way to phrase what I’m looking for on my dating site/app profiles.

I’m a guy and I’m in my 30s, but I’m not looking for a long-term relationship. Instead I’d like to explore more of the casual sex/dating/fun side of things (which I’ve never really done, so I’m not 100% sure exactly what I AM looking for).

I’m not looking to compulsively rack up notches on my bedpost — it’d be nice to have sex AND make friends — but I want to make it clear I’m not angling to be a boyfriend, while also not coming across like a guy who’ll say “wassup babe u dtf??” and send a d

k pic.

See? It seems easy to describe what I don’t want, but tricky to describe what I DO want. I suspect Captain Jack Harkness could say it with a wink, but I’ve got 500 characters to work with instead. Any ideas?

Swear To God, Not A Creep

DEAR SWEAR TO GOD, NOT A CREEP: t’s really not that difficult, STGNAC. Most of the time it’s about being honest about what you want and looking for people who’re on the same page as you.

Keeping things casual is more about behavior and attitude than anything else. In an online dating profile, f’rex, there’re a number of things that give a more “looking for a relationship” vibe than a “looking for friends-with-benefits”. If your profile is filled with photos of you playing with your nieces and nephews or talking about more “domestic” activities like cooking and such, you’re going to be giving more of an impression that you’re looking to settle down. At the opposite end of the spectrum, the dudes who have nothing but pics of them with their bros or finding excuses to get their shirts off to show their abs and talking about their crazy weekends are pretty demonstrably looking to get laid.

In your case, it’s pretty clear that you want to strike the balance between the two while leaning a wee bit more to the “casual sex” side of things. One of the things I’d suggest is leaving “long term dating” off your profile. Same with mentions of whether you want kids and the like. You can also say that you’re not looking for anything serious or just wanting to meet cool people and have fun… both of these are going to read more as “not looking for commitment”.

The other thing I would suggest is being playfully flirty in your messages back and forth. Maybe not right off the bat, but a little teasing, a little innuendo… these go a long way towards signaling intent without necessarily going overboard.

I’d suggest splitting your time between OKCupid and Tinder. Tinder may be more hook-up oriented, but there are plenty of people looking for something casual on OKC as well. Playing around with both will let you functionally A/B test your approach; what works on one app may or may not work as well on the other and you can adjust your profile accordingly.

And don’t forget: my book “When It Clicks” is great for helping refine your online dating game, regardless of whether you want something casual or more serious.

Good luck.

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