DEAR DR. NERDLOVE: I’m a 24 year old male from an expat family who moved to the Bay Area about three years ago from SE Asia and am now attending college as an undergrad.

American dating has mostly been an exercise in frustration for me, with success sprinkled here and there in the form of one off dates and even a three month mini-relationship. I could take you and the reader through the ups and downs of these various meetings but I want to avoid ossifying the entire Dr. NL readership so I’ll abstain. In any case, it’s the most recent girl I’ve been interested in that will be the focus of this letter.

I’ve been talking to (hanging out with, dating, labels are real fluid here) a cute, bright, driven 21 year old girl from one of my classes for the past week and a bit. We had talked before last semester but this is the first time we’ve really interacted on a personal level. We haven’t slept together, though we have made out, and it’s the issues surrounding this tension that I’d like to explore. See Doc, I think I’m what they call a square. I’ve always felt like a middle aged man trapped inside a young body; everything from my word choice to the way I dress makes me feel really out of touch with my class mates. This girl had to tell me what snapchat was and how to use it, and I’ve never felt older in my life. Another example was how I offered to walk her back to her flat (apartment) and she sarcastically quipped about what a gentleman I was. Do people not do this anymore?

The girl I’ve been seeing has never gone more than a fortnight without intimacy, and she’s been a pretty dedicated serial monogamist for a long time. Contrast this with a serious dearth of any activity on my part for the better portion of two years, and we have an issue. She is also into some kink and rough sex (choking, hitting, hair pulling, even to the point of bruising apparently), while I’ve had a very vanilla sexual history and I’m very slow and tender in bed (read, boring). It’s not that I have a fragile male ego that is threatened by her experience, on the contrary, I find it exciting and attractive.

The problem is she tends to point out and tease my squareness, and this makes me nervous around her, and of course that doesn’t make for comfortable making out. When we were kissing recently, she said I thought too much about the act and that I treated her like a china doll, and that she was into rough play. Of course upon hearing this, I got hella (new word I learned) nervous, and if anything became more incompetent. Another part of the equation is that she has had a string of fairly toxic and abusive relationships, and she tells me she doesn’t want to rush into something she’ll regret with me, ergo, no sleeping together until she feels comfortable with it.

So what we have is a situation where she’s hinting at me to be more masculine, more direct, and yet we’re holding off on sex. Now I absolutely don’t mind holding off on sex, but when it does happen, I’m really worried I’m going to disappoint her, and the longer we go without trying it and defusing the tension, the bigger the disappointment is going to be for her. I know good sex is about communication, but do you think this situation is resolvable? I’d like to add that I’m perfectly ok with changing my sexual style – I just don’t know whether I’ll be able to overcome that inculcated aversion to striking someone else, especially a woman.

I’ve never really though of myself as a prude until now. Am I, Doc? I know we have a sex positive feminist readership here, so I’m leaning towards the yes. I’d really like to expand my sexual horizons, I’m just horribly anxious about it and I feel like if it turns out to be a bad sexual experience and she calls the relationship, it will reinforce deeply held beliefs of mine about not being masculine enough.

Apologies for the wall of text, and I hope everyone who suffered through that has a good day.

– A Square in SF

DEAR A SQUARE IN SF: think the biggest problem here, ASSF, is that you keep describing yourself as being a loser and a square because… well, I’m not entirely sure. OK, so you haven’t had much sexual experience and you’re not terribly kinky. That’s not a bad thing, that’s not a good thing, that’s just how you roll. The fact that you’re framing these as a negative is causing more issues than the fact that you’re fairly vanilla; you’re setting yourself up to be uncomfortable and awkward because you think that you’re somehow deficient and inferior to someone who’s had more and/or different sex than you.

(Incidentally, I really dislike using “vanilla” to describe standard or non-kinky sex or people. Unfortunately, I have yet to find a good replacement for it. Anyone who has a suggestion for a different word is welcome to send them in to doc@doctornerdlove.com)

This actually gets into a common misconception people have when it comes to the topic of sex positivity; they assume that sex positivity is all about letting your freak flag fly and being into all kinds of outré and exotic kink and that people who aren’t into it are being sex negative. This isn’t true – sex positivity is about everyone being cool with what they’re into or not into, as long as it’s safe, sane and consensual. You’re straight vanilla? Awesome. You’re into being blindfolded and suspended from the ceiling by your nipples? Well, hope you’ve got safety measures built in, but ok cool, you do you. You’ve slept with a hundred people? Cool, high five! You’re a virgin? Cool, high five for you too!

But I digress…

The issue you’re having is primarily in your head; you’re so hung up on whether or not you CAN please this woman that you’re not giving yourself the chance to TRY. From everything you’ve said, she’s telling you how she wants you to kiss her – to be more aggressive and rougher. Now, if that’s just not your thing, then more power to you; odds are that the two of you aren’t going to be sexually compatible and you can just peace-out. But if it’s something you’re willing to give a shot… well, why aren’t you giving it a shot? She’s given you the green light. Are you afraid of not doing it perfectly off the bat? OK, I get that. Thing is, you don’t need to be perfect. The first time you have sex with someone isn’t a pass/fail audition that’s going to end the relationship if you don’t get it precisely right, especially if the two of you have been dating for a while before you sleep together. The first time with anyone is going to be awkward to one degree or another and 99.999% of adults understand that. Everyone has their patterns, their likes and dislikes that it takes a bit of practice to get your respective styles to mesh. Sometimes you synch up right off the bat because you’re pretty similar. Sometimes it takes a time or two and some awkward giggling to get things right. That’s not a flaw in somebody’s technique, that’s just sex. 

Your aversion to hitting someone is admirable, but as with most things in life, it requires context. You’re not striking a woman in anger, you’re being ASKED by someone to spank her and pull her hair because she gets off on it. It’s a very different situation.

(Choking is another matter, mostly because choking and breath play is INCREDIBLY GODDAMN DANGEROUS. That’s not varsity level sex, that’s a couple levels above varsity.)

So, how do you resolve this? Well, you use your words. You’ve not done anything like this before, so TELL her. Ask her what she wants you to do and then do it. She wants you to bite her? Cool, where? How hard? Done right, it’s a fun, sexy game; all you need is an open mind and a can-do attitude and a willingness to push your own envelope a little. If it works, then you’ve opened a new avenue for yourself – enjoy this sexual adventure. If it doesn’t work, then all that’s happened is that you’ve learned something about what you are and aren’t into and the people you’re compatible with. This doesn’t mean you’re a bad or boring or “unmasculine” (for bulls--t definitions of masculine), you just didn’t click with this person, which happens.

The only thing I would be careful about is how she treats your inexperience. You say that she teases you about being a “square”. As long as this is affectionate teasing, all is well; if she’s being mean about it or implying you’re a bad person for not being into the same things she’s into? That’s not cool and a pretty reliable sign that you should find someone who’s not an asshole about sex.

But in the meantime: use your words and take some risks. Ask her what she wants, to give you some pointers and try getting a little wilder.

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 in my early 50s and married. When I was 21, I saw a woman in a bar in New York and it was love at first sight. She blew me off that night. A year later I saw her in my hometown! I got to know her sister (who was not single) and we became friends. When I got to know my crush better, I found out that she was a remarkable woman, the smartest and wittiest woman I ever met (she later got an Ivy League PhD, so this is a legitimate statement). I wasn’t just smitten by her style, I was smitten by her intelligence. I was once an extreme nerd, so while we were friends, and there was a huge spark, she kept the flirtation going, but would not let it get physical. She married her boyfriend and when she had a baby, I decided to become serious with my girlfriend and got married myself.

At age 40 we reconnected online as long distance, only this time the sparks flew faster and hotter than anything I experienced in my life. She was literally “love bombing” me with compliments. We were both married, so we didn’t know how to handle this. She sent me over 500 emails that first year; it was a very serious flirtation, but she never let us get physical as long as she was married. The day she announced her divorce, I expressed my love for her and she told me it was too soon, but to keep doing everything the same for the next year.

Several months later things were getting weird. She introduced me to her parents and her kids, but she didn’t want us to get caught, so she wanted my wife there too. I begged to see her again, and this time she announced she had a new boyfriend — a complete disaster with multiple suicide attempts and arrests for violence. I was destroyed, completely and utterly destroyed. After quarreling for several weeks we decided to give our relationship a break for a year. Mind you, I was married, and she had a public boyfriend. After that year break, she denied we ever had a relationship. I was being gaslighted. I was hurt, confused, but still very much in love with the only woman who could touch my heart a certain way, and so every 1-2 months or so would send her an interesting email about our mutual friends. She would respond to many of them, but not all.

5 and 6 years after our “break up” she sent me two truly beautiful emails that left me with tears in my eyes, emails so beautiful that I felt buoyant for months. At that point, even though she’d been with her boyfriend for several years, it became clear to me that she was the only woman in the world who could really understanding me. She knew me, really knew what made me tick, and no other woman ever cared- not even my wife. You have to understand, she told me things more beautiful than any human being ever told me in my entire life. She helped me get through my father’s death in ways no other person did.

Years 7 and 8, I kept sending her emails, but she never wrote back. At Christmas in Year 8, I told her I couldn’t let myself look like I was obsessed, and that if she wanted to talk to me, she needed to just email me back. She never did. That was last year.

I can’t let go. I have never driven up to see her, I don’t compulsively send her emails, I have total control over my over actions. But inside my heart is filled with love for her and who she was from 2009-2017 and how she made me feel. Every day I wish we were together. I’m not an easy person to get to know or to understand. I’m a nerd. I met this person who was so special to me that I would have divorced my wife and left my kids to be with her. I am baffled why she would have seduced me and brought me to that decision and then once she had won my heart, gaslighted me.

I once had a therapist who told me that she was submissive and wanted a man to force her to cheat on her husband but when she and I got hot, I was too nice, too much of a boy scout and too nerdy for her to cheat on her husband with, so she chose this disgusting, dirty, violent individual to have a rebound relationship. But that she couldn’t officially let go of me because she was in love with me. This idea that I represented this honorable boy scout figure, someone she wanted to be the step-father of her kids, but not someone she found sexy.

But that’s the closest I’ve come to understanding what happened I need to be with her or I need closure.

Help.

This Is My Obsession

DEAR THIS IS MY OBSESSION: OK, I’m gonna be honest here. My initial reaction is “what the actual F--K is up with your therapist??” Because all of that? Not actually helpful. I’m pretty damn sure it’s also not true, but holy hopping sheep s--t, none of that’s useful or helpful for your recovery.

But instead, let’s talk earworms. You know: those moments when you get a song, especially a snippit of a song stuck in your head and you can’t dislodge it, no matter how hard you try. One of the reasons why earworms get stuck in our heads is because it’s an open loop. We’ve heard or remembered some piece of it — usually the hook, or some catchy part — but not the whole thing. Because we’ve only got that little piece of the song, it just goes around and around in our brains. Closing that loop — listening to the entire song — is one of the most effective ways of getting rid of an earworm.

So it is with relationships, especially ones that never actually happened. The reason why you can’t get over her is because, perversely, nothing ever actually happened between the two of you. This was a relationship in potentia, one that could be anything precisely because it never happened. That’s why you’re suffering. You’ve got a case of Oneitis. You’ve built this woman up so she’s no longer a person of flesh and blood, but a fantasy, and you’ve convinced yourself that she was perfect and the only person who could ever understand you. And the only reason why you can believe that is because… well, because you never got together at all. You never had to deal with the reality of her or dating her (or leaving your wife and kids for her).

Since the two of you never actually got together beyond flirting, this relationship can be anything you want it to be. It can be perfect because you’ve never had to deal with the reality of being with her. So no matter what is going on in your life, what your ideal relationship would be or look like, this fantasy relationship with your crush can shift and change right along with it. As a result: you have this eternally “perfect” relationship that seems to have forever been just out of your reach.

If you’d actually dated her… well, it’s impossible to say. Maybe you would’ve left your wife, married your crush and sailed off into the sunset together. Or maybe you would have had a brief fling, realized that you couldn’t make a relationship work and broken up. Or a combination of the two: you divorce your wife, marry her, only to have the cycle repeat down the line and you or she leaves for someone else. But regardless: it wouldn’t have been this vision of “perfection” that you’ve been holding onto for all this time.

But here’s the thing: this relationship was never actually going to happen. I don’t think she was a “submissive who wanted you to force her to cheat on her husband.”

(Seriously, WHAT THE F--K, yo?)

I think she was someone who enjoyed the attention you gave her, may even have liked you as a friend… but she was never actually attracted to you. Not in the way that you wanted her to be, certainly. Because here’s the thing: the people who want you and want to be with you? They’ll be with you. The idea of “Oh, I love you too much, but I can’t have you” is the stuff of bad fiction. It may take time before circumstances are right — or at least, less wrong — but people who’re genuinely into you aren’t going to string you along forever until telling you to piss off.

I’m gonna be honest here, my dude: her behavior sounds like someone who wanted attention and to be desired… especially if her marriage at the time was less than stellar. A “lover” who doesn’t pose an actual threat to the relationship but will give her all the thrill of being wanted or lusted after can be a hell of a thing. But once she was divorced and that barrier between you was removed? Well… she didn’t want anything more than the fantasy. Hence: keeping you at a distance, until she ended up with a new boyfriend, walking disaster or not.

(And, completely unrelated: yeah, telling someone how much you love them right when their divorce is finalized is too soon. Even someone who’s long over that marriage is gonna want to give themselves some time instead of rushing into something new.)

The reason why she denied you two had a relationship? That, I strongly suspect, comes down to the two of you having very different views of how things were between you, mixed in with the fact that you never took “I’m married/ you’re married/ I’m dating someone else now” as an answer. By the time y’all took that “break”, it was pretty clear that you were way the f--k more invested in this than she was and she was likely getting to the point of trying to dial things back. By the point that she wasn’t responding at all? That was your sign that it was over. Holding on for three more years was honestly, just torturing yourself for no good reason.

Now I know all of this hurts, and I’m not saying it to be cruel. I’m saying it so that you understand that what you’re mourning is a fantasy. What you had was much more complicated, much more nuanced and far, far less perfect. The reason you can’t let go is because you’re still experiencing it as the fantasy, which is what’s giving you that open loop, that earworm. Recognizing the relationship for what it was will help you close the loop and let it go. 

But to do that, you need to forgive yourself. Part of seeing the relationship for what it actually was is going to leave you feeling like a fool or an idiot. You aren’t, and you weren’t. What you were — and still are — is someone who loved not too wisely, but too well. Forgive yourself for being a fool for love, like so many of us are. Forgive yourself for giving so much of yourself to someone who wouldn’t give back. And forgive yourself for the time you spent on your crush — time that took you away from your family.

And while you’re at it? It’s time to make things right with your wife and kids. Let’s be honest here: you were neglecting them for your Oneitis, taking time and love away from them to throw down the hole of this fantasy. That’s a cruel thing to do to people who love you. It would have honestly been kinder to get a divorce, even if you didn’t immediately leap into something with your crush. At least then your family could’ve gotten closure on their end.

What does making things right mean? That’s up to you. Maybe it means redoubling on your relationship with them and being the husband and father you should’ve been. Maybe it means actually leaving, so that things aren’t prolonged any further. But you have a much bigger obligation to them than you do to the memory of the one that didn’t just get away, but was never going to happen in the first place.

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’m a man in my 30s with next to none sexual experience. There are various reasons for my lack of experience, but I think the main reason is that I’m far too picky, when you consider my own attractiveness. The lack of sex in my life has bothered me quite frequently, and the only reason I haven’t visited a sex worker yet is that I’m morbidly afraid of STDs. Herpes, to be more precise. I understand that most people will contract HSV-1 during their lifetime, and HSV-2 too is quite widespread. I also understand that most infections are asymptomatic and when they aren’t, the symptoms are mostly manageable. Still, because of my kissless and sexless life, I have been able to count myself among, for lack of a better word, the clean ones (not trying to shame of stigmatise, you can probably tell that English isn’t my first language), and this has been a great source of joy in my life. Now I’m afraid that I have thrown it away for nothing.

I recently met a woman in a bar (unlike much of the world we aren’t under lockdown) that for some reason seemed to be quite infatuated with me. At some point she asked if I would like to have sex with her and I thought why not, she was good company and attractive enough. Or so I thought, since it turned out that I wasn’t nearly as aroused by her that I thought I would be. I couldn’t maintain an erection and all our attempts to have intercourse more or less failed. I ended up fingering her and although she seemed to enjoy herself, I felt a little bad for wasting her time.

I would be more than able to laugh the whole incident off, if it wasn’t for the health aspect. I don’t claim to be the greatest judge of character, but she seemed like someone who would have a rather active sex life. I’m not judging, that just would make her more likely to carry the viruses I dread. I think it’s needless to say that I wore a condom and I was under the impression that the risk of catching herpes during dormant periods is somewhat low. I haven’t had any symptoms yet, but I’m not sure if it makes me feel any better. Asymptomatic herpes isn’t usually tested here, so I pretty much have no way of knowing if I’m as healthy as I used to be. And this makes me feel awfully dirty. Not to mention, now I have started to see crabs everywhere.

I see little reason why I would be having sex on a regular basis from now on. I have a extremely high sex drive, but it also seems like I see sex as something inherently disgusting. I think I would need a perfect partner to get over the dirtiness of the act. Now I feel like I have traded the only pro of having no sex life for the worst con of having one. Because of a momentary lapse of judgment I went from somebody who had zero partners to somebody who has fifty, and only thing I have to show for it is an experience I could have lived without. I used to think that I had a rather relaxed attitude towards sex, but it seems I’m not nearly as open minded as I thought I was. I’m not sure how much better I would feel if I had enjoyed the experience, but I’m sure I would feel far better if I had shared it with somebody I would perceive more chaste, and this bothers me somewhat.

Any any advice how to cope with this all would be appreciated

Not Trying To Be Dramatic But Did I Ruin My Life For Nothing

DEAR NOT TRYING TO BE DRAMATIC: First and foremost, NTBD: I think you should talk to a therapist. That level of obsession and those intrusive thoughts sound an awful lot like a form of obsessive-compulsive disorder. That’s something that’s best addressed by a psychologist, who can help provide answers and courses of treatment that can help get those thoughts and fears under control.

But whether it IS a form of OCD or not… hoo boy.

So let’s cut right to the chase. First of all: the odds that you caught herpes from this person are pretty minimal. Second of all: your problem isn’t that you “ruined your life”, it’s that you’re obsessing about herpes to the point that you’re giving yourself a breakdown.

Regardless of whether you’re suffering from an emotional disorder or not, you’ve assigned a moral judgment to sex and sexuality and that being “the clean ones” is somehow a mark of your superiority. Except… it’s not. A viral infection is inherently outside of morality; it doesn’t mean anything except that you’d been exposed to the virus. Not having HSV-1 or HSV-2 doesn’t make you any better or worse than someone who does have it. It just means, quite literally, that you haven’t come in contact with the virus. Period.

The same is true for whether or not somebody’s a virgin or whether they’ve had sex: all it means is that somebody has had a particular experience. The number of partners they’ve had is equally, ultimately irrelevant as to whether they’re a good person or bad person. There’re folks who could qualify for sainthood who’ve had dozens or even hundreds of partners. There’re mass-murderers who have never touched another person’s genitals in any way, shape or form. Assigning value to someone based on serostatus is, ultimately, a bulls--t idea… especially when we’re talking about an infection like HSV-1 or HSV-2. Between the percentage of the population who’ve been exposed to either virus, the fact that most people who have herpes are entirely unaware of it and the fact that herpes is just a skin condition, treating having herpes like a world-shattering event is frankly, stigmatizing horsef--kery.

And let’s be real here, that’s what you’ve done. You’ve elevated the idea of having a cold sore to a “life-ruining event” based on what’s ultimately a moralistic value. While I realize English isn’t your first language, the way you describe things and the words you choose are incredibly telling. “One of the clean ones”. “Dirty”, “perfect partner”… That’s all pretty f--ked up, dude, especially considering the number of people in your life — including your parents, your friends and co-workers — who very well may have the virus and not know it.

And here’s the thing: you should honestly know better. It’s pretty clear that you’ve done your research about herpes as an STI. But it doesn’t seem clear to me that the truth of the matter has actually sunk in: that herpes is ultimately an inconvenience. An outbreak can be painful and annoying. A cold sore isn’t going to be all that aesthetically pleasing to look at. But the worst case scenario for having herpes is… more frequent breakouts. That’s it. Painful, unsightly, and it means a brief period of abstinence, but those are fairly minor in the scheme of things.

Your attitude, however, is the problem. The way that you’re treating both the possibility of having herpes or the possibility that someone else does, actually increases the odds of being exposed to the virus. Because the stigma surrounding herpes is so high — vastly outweighing the actual effects of having the infection — people are less likely to get tested, less likely to get treatment and less likely to disclose to potential partners. If people don’t get tested, they have no way of knowing if they’re carrying the virus or not. If they don’t know, they can’t get treatment, which not only lessens the frequency and severity of outbreaks, but also decreases the chances of transmission. And by creating an atmosphere where people are less likely to disclose that they have herpes, then they and their partners are less likely to take precautions that would help prevent the spread of the disease. That, in turn, increases the knock-on effects of having been exposed to HSV-1 or 2. I’ve seen couples go through hell because one of them had an outbreak, leading them to be absolutely convinced that their partner must have cheated. In reality: one of them had been exposed in a previous relationship, and simply had no idea that they had it at all. But all that heartache and trauma they went through came about because we treat it as “something that ruins your life forever.”

And, I mean, let’s look at your reaction here. First, you’re making all kinds of assumptions about your partner based on… well, nothing at all, other than you and she went to bed together. Maybe she has had an active sex life. Or maybe you’re the third or fourth person she’s ever slept with. You have no idea; you’re basing all of this on hypotheticals and things that you’ve conjured up out of thin air. That goes hand-in-hand with the whole “I’ve gone from someone who’s had zero partners to someone who’s had 50.”  No you didn’t, dude. That whole “you’re sleeping with everyone they ever slept with” is sex-shame-y horse-s--t that got spread around at the height of the AIDS crisis and is mostly used to justify abstinence-only education. Not only is it not actual risk-assessment, it’s not even accurate. If someone were going around banging everyone who said “yeah sure why not” and not using a condom, EVER… sure, we can say that he’s slept with everyone that his partners have ever slept with. But someone who’s getting tested regularly so they know to get treated if they do pick up an infection and making sure to use condoms every time, then the only person they’re sleeping with is the person they’re actually in bed with.

And if they and their partner are in a mutually monogamous relationship? Then that loop is closed entirely.

Here’s what you need to do. First of all: go get tested for STIs. Make sure that you ask for the full battery, including herpes. NOT because your one hook-up might have infected you, but because it’s what responsible, sexually active people do. Getting tested means you can get treated, and it means you aren’t at risk of spreading any infections to your future partners. Next: watch Ella Dawson’s TED talk about herpes and dating, followed by reading up on what Planned Parenthood has to say about herpes and safe sex practices in general so that you can have the facts. Then, like I said: go talk to a counselor. The level of terror this is inspiring in you is neither productive, nor healthy.  All it’s doing is making you miserable and cutting you off from relationships or even just simple pleasure in your life.

I get not wanting to contract an STI. Herpes may not be a big deal, but it’s entirely legitimate and understandable that you’d rather not catch it. But the fact of the matter is that life is a full-contact sport. Everything you do comes with risks. You take risks walking out your front door in the morning. You take risks when you eat a sandwich, commute to work or, yes, have sex. Part of living is understanding and managing those risks, deciding which are acceptable and how to mitigate them where you can. Right now, you’re letting your fear and your judgement paralyze you. Talking to a therapist can help you get past those fears and actually let you enjoy your life and the full cabaret it offers you.

Get those fears and thoughts under control, man. You’ll be much happier.

Good luck.

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