DEAR DR. NERDLOVE: I’m a 34 year old male. I’ve never kissed, sex, relationship, etc… I don’t mind discussing this with people I know. I feel like because I’m too open about my situation people think I’m looking for self pity. I don’t really, I just want them to know about my situation so it’s not awkward when it comes up later in time. I’m not embarrassed, but I know that some people look at as a red flag… especially women. So my question is : Is my openness about my situation really a redflag/dealbreaker? I’m not good with secrets. I also think I use it as an excuse when I get the vibe they don’t understand me.

Too Much Information?

DEAR TOO MUCH INFORMATION: The question you’re asking isn’t necessarily the question you think you’re asking, TMI.

I’ve talked a lot about the bulls

t shame that men get about virginity and sexual inexperience and how that ties into toxic definitions of masculinity and how experience or inexperience isn’t something to be ashamed of. That being said: much like people who misuse the term sex-positive means (or misunderstand what it means), there’s a difference between not being ashamed and inappropriate sharing.

See, one of the things that we look for in friends and partners is emotional and social intelligence: whether they understand social rules, know when it’s appropriate to discuss things and when it isn’t and – critically – what information people don’t necessarily need to know. People who don’t conform to the expected social rules make us uncomfortable; sometimes it’s simply a matter of informing us of things that we don’t want to know, other times it’s a question of “if they don’t get this rule, what other, more important rules do they not get?” So when you’re sharing incredibly personal things about yourself – such as being an older virgin – the question isn’t always about what you’re sharing but when.

If you’re just blurting this information out during the “getting to know you” phase of a date or interacting with your co-workers… well, that’s generally not the right time. You’re telling people far more about yourself than they want to know, never mind need to, and usually at a time when it’s not socially appropriate. If you’re talking about sex or past relationships, that’s one thing. If you’re just dropping this truth-bomb in the middle of a conversation, a “Just FYI, I’ve never had someone else touch my penis. So about those Spurs…”, well that’s just going to be weird.

There’s also the question of how much of this you’re sharing. Not everyone needs to get the full disclosure about your sexual history (or lack thereof). You’re not giving a deposition, you’re having a conversation. You can just leave it as “yeah, I haven’t dated much” or “I’ve never had a serious girlfriend/boyfriend”; most of the time that’s all anyone wants to know. If they want to know more, they’ll ask and then you can go into more detail. When and if someone should know more – such as when you’re about to get busy – then you can tell them more. But even then, a simple “just so you know, I’ve never done this before,” tends to work better than a sudden and unexpected download about the hows and whys of your sexual history.

And as always: how you talk about it is important. People will follow your lead when you talk about yourself. If you’re revealing that you’re inexperienced like it’s a giant flaw, then people will respond like it’s a giant personal flaw. If you roll it out like it’s no big deal, it’s just part of who you are, then they’ll treat it like it’s no big deal. And if they do get weird about it… well that tells you a lot about them, doesn’t it? If someone sees your experience or lack thereof as a deal-breaker, then that’s their problem and they’ve just self-selected as someone you wouldn’t want to date anyway.

Good luck.

DEAR DR. NERDLOVE: I’d love it if you could shed some light on my situation, you always make sense and I appreciate how much you take lots of angles and even a meta-perspective into account usually. I’m a young woman in my mid twenties. I have a fulfilling life: lots of hobbies and interests, a good career, I’m always on the lookout to travel, I have moved to different cities because of studies/jobs a lot while maintaining close relationships with my family and friends, I love to learn and think about new stuff all the time. I’m a bit of a free spirit and I identify as polyamourous. (I can cite some passages from “the ethical slut” and other literature on the subject by heart and have internalized and lived by its values). I’ve had an open relationship in the past, where I had one “boyfriend” and 1-2 “mini-relationships”. My boyfriend had the occasional “extra-curricular activity”. It worked for us that way, things ended a year ago for reasons that had nothing to do with being open/poly.

Now “the problem”: a few months ago I met a guy who is a few years younger and we hit it off right away: we love talking about the same topics, we both love to travel, we have heaps of fun together, we just vibe very well. One drunk night we landed it bed together and, you can guess it, had sex. A week later, I discovered that I took his virginity that night, without knowing it at the time of the act. We talked about how I felt bad because it wouldn’t have happened like that if I had known that beforehand. He said he had no regrets and didn’t want to say anything because he thought it wouldn’t have happened otherwise. (He has a point there, but I still feel taken advantage of and like I took advantage of him at the same time as well). We then had the “what are we talk”. It was clear to him from the get-go that I am poly and that we could build a loving friendship but without being exclusive. He understood, asked the right questions, we talked about “the rules”. Everything is still going fantastic in the 2 months we’ve been together now. We still vibe well, enjoy our time together (even though we live 100 miles apart), talk about feelings/issues, he buys me gifts, we do fun trips, he introduced me to his friends and family (I didn’t introduce him to family because that’s not something I do). Even though I am his first girlfriend, he just gets everything right about communication etc., which just proves again what a great human being he is.

And that is my “problem”: it is going so well, that I am confused. He makes me want all those mundane, typical societal things I’ve looked down on for so long: suddenly I’d like to settle in something typical and exclusive and couple-y – even though that is in direct conflict with everything I have believed in and stood for in the past and have defended with reason and fire against nay-sayers about open relationships.

Please help:

– Should I go against my nature and try being exclusive? How do I even bring that up, after it took a lot of conversation to explain polygamy to him in the first place? Is he even going to want monogamy, perhaps he likes me that much because of my poly-nature?

– Will it affect our relationship for the worse? maybe it goes so well because we only see each other sporadically (because of the distance)?

– Sometimes I feel like I am using him because I am older and more experienced in the sexual and relationship department – any thoughts on that? Is being poly with someone like that even fair? Can he really make a good estimation on the topic if he never had a girlfriend before?

Please help – suddenly everything I was so sure of isn’t that sure anymore. My thoughts need some structure.

Thanks in advance!

Cheerfully Confused

DEAR CHEERFULLY CONFUSED: I think you’re making things more complicated than they need to be, CC.

Here’s the wonderful thing about people: they’re complicated and complex. We lay down these rules and labels, many of which are absolutely arbitrary, and then freak out when we realize that they’re not perfectly universal. We grow and change and find people who push us out of our comfort zones and into worlds that we never thought would apply to us and then we get scared because suddenly everything is different. The problem is when we tense up and try to force things into ill-fitting labels and rules instead of just going with the flow and seeing where things take us.

Right now you’ve got a boyfriend who’s making you think all kinds of thoughts that are contrary to how you’ve defined yourself. You’ve always been poly and now you’re thinking about being exclusive… ok, and? You’re allowed to try different relationship formats as long as your partner or partners are down with it. Maybe you’re in a more monogamous period of your life. Maybe this particular relationship with this particular guy is just an exception to your general rules. Or maybe this is just a temporary thing and it will pass as your relationship grows and matures. The key is to not freak out about it. This doesn’t mean that you were wrong to be poly or that there’s something more “correct” about monogamy… it just means this is where you are right now. If you’re down with giving exclusivity a shot, then hell, go for it. You and your partner or partners have the right to set the rules of your relationship as you see fit.

(That being said, experimenting with exclusivity for the first time in a long-distance relationship makes an already difficult relationship even more difficult, so be prepared.)

It’s admirable that you’re concerned about using him or leveraging his inexperience against him, and that’s a sign that you’re a good, ethical and caring lover. Users and abusers don’t concern themselves with such questions. You should keep in mind that no relationship is going to be perfectly balanced and egalitarian. There’s always going to be one partner who has more experience than the other. Nobody is going to have the exact same history or experiences as their lovers; that’s just how the world is. The key is not using that differential as a weapon, and believe me, the less-experienced partner is just as capable of wielding that whip as the more experienced one. Don’t assume that just because he hasn’t seen or done as much as you have that he’s incapable of making decisions for himself. He’s a big boy and he’s perfectly qualified to decide what sort of relationship he wants to try.

The way that you make things work – as is true in every relationship – is communication, communication, communication. As I’m always telling people, the answers to most relationship difficulties is to use your words. Every relationship is an ongoing conversation, after all.

Case in point: the poly vs. monogamy question You’ve talked about being poly before and what it means, so now talk about monogamy. Explain how you’re feeling and ask how he feels about it. If you’re both into the idea, then have a discussion about how you both see it working and what the rules should be. Perhaps you would want to treat this as a timed trial – see how monogamy works for a couple months and then revisit the question. Perhaps you’d want to try a semi-monogamous commitment; some activities such as penetrative sex are off the table but other things are permitted.

Just don’t spend the emotional and mental bandwidth looking for reasons why things are about to go wrong. The worst thing you can do in a happy relationship is waste it waiting for the other shoe to drop. When you’re borrowing trouble from the future, you make it impossible to enjoy the now.

Keep those lines of communication open with your guy and don’t sweat the labels. Your relationship can be whatever you two decide it is.

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 was a very late bloomer during my teenage years. As a result, it took me a long time to develop an interest in the ladies. To add up to the problem, I’m very introverted as well. I have also had some bad luck with the people I have been interested in labeling me as “just a friend”. The result: I have never done anything with women beyond maybe some hugs. No kissing, or sex.

I got into college a little late (I was 27). Went through a few semesters without friends, just acquaintances. Finally, 2 years in, I met a few people. I developed a crush on one of the girls, but she had a boyfriend at the time. I figured things were finally looking up for me; I could maybe meet more people through these friends. Maybe meet a girl somewhere inbetween?

After a semester with them, things started to derail. One of them dropped his course, another girl started dating a guy and quit the group. The girl with the boyfriend moved. I was alone again.

I kept in touch with the girl I had a crush on. She told me she broke up with her boyfriend, and, well, I got a bad case of oneitis; I started going after her pretty hard, even offering to visit her in her new city just so I could try something and at least get the kiss part over with.

Turns out she wasn’t that fond of the idea. I had to get three soft-no’s to get a grip. It sucked, but then it dawned to me that I was back at square one.

I don’t really know how to do much about dating. I’m currently trying tinder and other dating apps, and while I do get matches, I’m bad at escalating things. Sometimes I’ll message for too long and get unmatched. Sometimes I’ll get ghosted. I went for a walk with a girl from tinder one time. While I enjoyed it, I chickened out and didn’t really try anything other than talking (I’m a great listener). It makes me feel really awkward and terrible that I don’t know how to do these basic things at my age.

I’m kind of thorn about this. Half the time I’ll understand this was mostly due to my lack of attitude, some outside factors, past history, etc, and that there are things I can do about it now… but the other half I wonder if there’s something wrong with me. I mostly worry that, if I do meet someone, they might not understand and reject me, or label me under “weird”.

I have even looked up escorts online (but didn’t message them) to maybe get it over with, but I’m not sure how to go about it, or if it will even help me in the first place.

Help me out, Doc

Misfit-But-Still-Collectible-Toy

DEAR MISFIT BUT STILL COLLECTIBLE TOY: Let me help you with something that may put your mind at ease: you’re going through the exact same thing that literally everybody goes through when it comes to dating. Everybody starts from zero. Nobody comes to dating or relationships with an instruction manual. Hell, that is literally why I write this column: to provide that instruction that people wish they’d had growing up.

Everybody starts out with no experience and has to fumble their way forward. If you’re lucky, you might have a role-model who you can look to for advice or guidance. Some people are extremely lucky to have a natural gift with human interaction. But even they have to crawl before they walk and walk before they run. And – as everyone can tell you – learning to walk and running means falling over a lot in the process.

If you want to learn to walk, you’re going to have to let yourself fall a few times. Maybe even a lot. You’re going to pick up some bruises, same as everyone else did, but those bruises are signs that you’re trying things. You’re pushing yourself. You’re taking risks. Sometimes those risks are ill-advised, like your oneitisget the best of you. But you learned and now you know better.

And let’s be real here: you’re obviously doing some things right. You’re getting matches, you’re getting dates. That’s pretty damn good. Ghosting happens, regardless of your experience. Dates to nowhere happen. That’s just part of the dating experience for everybody.

Your biggest problem, to be honest is that you need to take more risks, MBSCT. You have to be willing to court rejection and failure because failure is part of how we learn. Now, this doesn’t mean that you should dive into things head first. You don’t need to, say, go for a kiss in the first 10 minutes of a date because screw it why not. But you should stop hesitating or waiting for 100% certainty for things. You’ve had a few good back-and-forths on Tinder? Time to ask them for a date. Things are going well on a date? Ask her for a second. She’s giving the “I want to kiss you” signs? Tell her you want to kiss her and see what happens. If you get rejected… well, it sucks, but you took that risk. Each chance you take makes the next one that much easier. You learn a little more about what to look for and – critically – that you can take that chance and survive. 

And sometimes when you fall, you fly.

You may be starting a little later than average, but that’s not a bad thing. You’re not in a race or a competition with anybody, you’re on a journey. You don’t have a deadline. You don’t need to catch up to anyone. You just need to get where you’re going, in your own time and at your own pace.

You’ll be fine.

Good luck.

DEAR DR. NERDLOVE: I am a 21 year old woman living and studying in the United Kingdom, and I wondered if you could answer a question for me.

I’m currently single and happy to be so. I enjoy the company of friends and family, but am quite introverted and enjoy being alone.

I dated a guy for a few months a couple of years ago, but I wasn’t so keen and we broke it off. I have never had any kind sexual intimacy with a partner before, but I’m very aware of my desires and drive and curious about having sex. I don’t identify as any sexuality; I just don’t know yet.

My question is; if I ever pulled at a bar or a club, would it be a good idea to sleep with them?

First of all, twenty-one may be seen as pretty old for being a virgin, and will probably put them off. And while I want to have sex in theory, I’m sure I’d be pretty scared if it ever actually happened. This person could well be a stranger, and I wouldn’t know who they were or what they could do. I have been diagnosed with GAD, and am pretty sure that I probably have a lot of social anxiety.

If going out with mates can sometimes be difficult, the idea of intimacy seems almost impossible. Friends and peers who have had sex make it sound really easy, like breathing, and I’m often surprised when they say how young they were when they had their first time (nothing illegal or shocking, btw)! I feel like i must have been off sick when they had that lesson.

I also have quite a quirky personality. I’m pretty nerdy and bookish, but enjoy wearing make-up and keeping in shape. I like to crack a lot of jokes, talk about odd things, and make people around me laugh. I doubt, however, that these things make me particularly sexy.

So this is just a question more than anything. I’m not as I’m saying this about to hit the town, so I guess it’s kind of hypothetical. And to be honest; I think I know what your answer would be; wait until I’m in a relationship with someone I’m comfortable with and then see how it goes. Thing is, I’m not even sure if I feel romantic attraction as I’ve never really had a crush on anyone I’ve known. I dated my ex because he seemed like a lovely guy and I wanted to give it a go.

I have to admit, that this question is mostly fueled by my libido, and that’s never a great start. I’m not ready to be in a serious relationship right now; I have enough to worry about in terms of study and getting a job as it is.

I guess what I’m asking is if I really, really wanted to take the plunge and take someone home, how could I go about doing it, and what could I do to keep safe?

Sorry for the weird question. The writing probably sounds a bit formal, and to be honest, I feel odd for asking. I don’t think people see me as being a very sexual person on the outside, and I probably flatter myself by making it sound like getting another’s interest would be easy in the first place.

Thank you for bearing with me,

Girl In An Oyster Shell

DEAR GIRL IN AN OYSTER SHELL: Let’s start with an obvious question, GIAOS: do you want to have sex? Is this an actual need that you’re feeling and you are starting to ache to fulfill it? Is it more of a curiosity, wanting to know what you’re missing? Is it something that’d be nice, but something you could live without if necessary?

What I would suggest hinges a little on those answers. Sexuality is less of a spectrum and more of a Japanese multi-axis graph; some people get incredibly horny but as a slow-burn for specific individuals. Others are voraciously omnisexual, still others don’t have a sex-drive at all. Some crave members of one gender but will sleep with members of a different gender if they’re sufficiently hard up.

So if you’re demisexual, for example, it’s not going to do you much good to go trawling bars and clubs for a hook-up. Just something to consider while you’re pondering your options.

Meanwhile, let’s talk about some of your fears and anxieties for a second. The first is that at 21, you’re behind the curve for sexuality and people will judge you for it. And while this may be true – assholes are everywhere after all – there are guys out there who aren’t going to see this as being bad or a deal breaker. The folks who treat your being a virgin as something shameful or unusual are self-selecting out of your dating pool and your bed.

As for strangers… yeah, that’s a risk. That’s a risk everyone takes when it comes to sex and dating. You help mitigate those risks by being aware of them, understanding your vulnerabilities and correcting for them as best you can. You keep your bulls

t detector fine-tuned, you watch for danger signs. If you don’t necessarily trust your judgement, then you have friends who can help you vet potential candidates. Sex is a full-contact sport and comes with inherent risks, same as snowboarding or skiing. You go in using best practices and safety procedures and do your best.

Now, all that having been said, there is a fairly simple answer to your dilemma, GIAOS: don’t look to hooking up with a stranger for your first time. You may well want to look to some of the guys you alreadyknow instead. Presumably you know them well enough to know which ones are the most respectful and trustworthy. You’re already comfortable with them – you have that pre-existing friendship – which makes talking to them and being relaxed around them easier. That alone makes them better potential partners than rolling the dice on Johnny Rando from the bar.

There’s also an advantage to looking to friends you know than someone you pulled on a night out: they’re more likely to actually know what they’re doing and make an effort to please you, especially if they’re agreeing to be your first time. One of the reasons why a lot of women don’t care for casual sex is because the sex is so rarely worth it. Most guys will get off in a casual encounter; far fewer women will.Someone who knows you, respects you and is invested in your comfort and pleasure is going to be a better lover than someone who’s just looking to bust a nut and call it a night.

So consider picking a single guy friend you trust and find attractive and tell him that you want some no-strings, time-to-lose-your-virginity sex and is he down to get down?

This approach can have drawbacks; there’re folks who’re just bad at keeping things casual. Some guys have a hard time seeing sex – especially sex with a friend – as being just about sex for sex’s sake and get awkward about it. And even people you know well can have a bad case of Crouching Good Guy, Hidden Douchebag.

But overall, there’re fewer risks to looking to a friend for a casual one-off, especially if all you want is to get the virginity thing taken care of.

Or, if it’s more your speed, go on some dates, vet some dudes and see if you feel good about giving them a shot. It can take a bit longer, especially if you’re looking for something more hit-it-and-quit-it, but it’s the more common approach.

All up to you and what feels like the right approach for you.

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: First off, I’m a big fan – I’ve been following your website and YouTube channel for over a year now, and I’ve also read your book New Game+. I work as a psychologist, and I would say that a lot of your advice is very sound and follows the same principles I’ll use when working with clients. My question is around desiring women who you might not be compatible with.

Long story short, I think I’m a fairly desirable person; I’m fairly good looking (24 years old), I’m completing a PhD, I’ve competed in outdoor sports for over 10 years, I play an instrument, I’ve travelled and lived in several countries (on the flipside, nowadays I spend most of my days working late amongst grey-haired academics!). I KNOW how to talk to people and make a connection, and I know the importance of practising positivity in your daily outlook on life. Two years ago I broke up with my girlfriend (who was almost 10 years older than me, held a PhD) – I thought I wanted to marry her, but for several reasons I decided I wasn’t happy being with her. Since then, I found out she’s moved on, and I’ve accordingly developed a bad case of Oneitis, wishing I’d never broken up with her!

When the relationship ended I was determined to ‘play the field’ (I had a conservative upbringing and didn’t indulge in hedonic desires… until I came to my senses in my 20’s!). I’ve always had fantasies of being with a stream of fit, attractive, young women who I’m surrounded by at university everyday. However, my success in this venture has been zero – in fact, I’ve had sex once in 2 years, with someone who I was not even that attracted to as a person.

I’m stuck. I feel as though every time I make an attempt at speaking or flirting with these young, attractive women in their 20’s, they’re either A) uninterested, or B) think I’m weird as hell (I suppose I am a little bit ‘quirky’; I’m like the living incarnation of Dr Frasier Crane or Ross Geller). The flipside of this is that I often find THEM utterly boring or juvenile (but hot nonetheless!). Recently, I met a woman who is in her late 30’s who is actually very interesting and I get on with well… (an academic, moderately attractive), but I feel as though if I started dating her, I will be ‘disappointing myself’ by ‘giving up’ and not managing to sleep with the young women I ‘should be sleeping with’.

Here comes a longer stream of irrational beliefs: I feel like I haven’t had the dating life I’ve wanted my entire life. I don’t feel like any of my girlfriends or one-night stands were super attractive – I frequently lust after the gorgeous girls I see around me, but even the ‘thought’ of having sex with them seems impossible. I have never been able to ‘sow my wild oats’; I hear stories of ‘everyone’ around me who has slept with 10+ women, or people who are just ‘sleeping around’ as if it’s no big deal – and this causes me a great deal of anxiety and uncertainty in myself.

I have become obsessed with this feeling of ‘inadequacy’; like I’m somehow not good enough, or I’m missing out on all the sex that all the other good-looking people are having. I’d like to be able to look back upon my younger days and say “I slept with 10 girls, and I had the ability within me to have casual sex with beautiful women”.

I suppose I feel a bit like a failure at sex and dating, but I’m also conscious that I may be going for the ‘wrong types’ of girls? Perhaps Dr Frasier Crane shouldn’t be going for fit young 20 year olds, but should be going for the well-travelled 30 year old academics? Maybe this is a case of identity crises – a person who is caught between wanting to be a ‘young athletic man’ and a ‘grey haired academic’?

Any advice (or assistance with irrational thinking!) is greatly appreciated!

Yours, 

Be The Ball

DEAR BE THE BALL: There’s a lot to unpack here. Let’s start with the fact that you’re young, dude. Most of what you’re hearing about “everyone” around you banging out like rabbits on a meth binge is exaggeration and confirmation bias. Yeah, folks sleep around… but it’s hardly a case that you’re the last American virgin being left behind as everyone has marathon orgies. The lifetime average number of sexual partners for most people is around 7 or so. The fact that you’ve had three partners thus far – that you’ve mentioned, in any case – puts you pretty firmly on course to be in the center of that particular bell curve. More importantly though is that focusing on numbers is a great way to make yourself miserable in short order.

But I’ll come back to that in a second.

Instead, let’s talk a little about how you identify, because you’ve picked two very different archetypes. Frasier Crane isn’t what most people would call “quirky”.  “Prissy”, maybe. “Snobbish” for sure. “A bit up his own ass,” wouldn’t be off either. Frasier is a virtual living stereotype of the Harvard-educated elitist with the benefit of money to back up his tastes. Ross on the other hand… look, let’s just go with “Ross is the worst” and leave it there.

I think what you mean is that you’re something of what other people might call “an old soul”. It sounds like you have more life experience than the average bear in their early 20s – which is actually a plus in the attraction department. However, it also means that you’re going to be in a different stage of life than a lot of people your age. The average age of PhD candidates is 33; most people in their early to mid 20s have just gotten their undergraduate degree and are trying to decide what to do next.

Your early and mid 20s tend to be the years of discovery; you’re dealing with adult responsibilities (for the first time, for many) yet often still have the drive and interests of the young.

That stage of life issue is going to be pretty crucial. One of the reasons I’m a believer in the old rule of thumb that the youngest one can date is “half your age plus 7” is because this keeps you relatively within the rage of someone who’s had similar life experiences. As someone who just crested over 40, I personally find the idea of trying to seriously date someone under the age of 27 to be mind-bogging at best; ignoring the lack of shared cultural touchstones, we’d be in such different places in life it might be hard to make plans in the first place.

Now the reason I bring this up is because similarities are an important part of attraction. The more you have in common with someone, the more you’re going to be attracted to them. This includes things like shared interests, educational levels and social outlook. This is something that a lot of folks overlook: no matter how hot somebody is, if you can’t have a decent conversation with them, it’s really hard to have satisfying sex with ’em.

Believe me. I’ve tried.

A lot.

So therein is going to be part of your dilemma; if you can’t really relate to the young hardbodies you see wandering around, you’re going to have a hard time trying to bed them.

But this isn’t the issue so much as your attitude about it. You, like a lot of guys, have bought into the idea that you’re “supposed” to be having certain kinds of sex – that wild, no-strings sex that everyone else SEEMS to be having at the drop of a hat. And while that’s not a bad thing if that’s what you want, it sounds to me less like you actually want this and more that you feel like you should be capable of it. It seems to me less that this is an actual need so much as a desire to be someone who could have that kind of sex – a bragging point to shore up your masculine bona fides rather than just being someone who likes to screw.

And that… isn’t so healthy. Trying to screw around to prove a point – whether it’s your virility, your desirability or just old-fashioned validation is a great way to not just frustrate yourself but to frustrate yourself and tie your self-worth to things outside of your control. When you fail to get laid, your self-esteem drops into the crapper and when you do succeed… well the sex is rarely actually worth it. In fact a lot of it kind of sucks. You end up sleeping with people who may be traditionally attractive but don’t actually do anything for you. That’s a recipe for the walk of shame afterwards, asking yourself “why did I even bother?” To add insult to injury is that it doesn’t even make you feel better. You won’t feel more satisfied or more manly. In fact, the fact that it hasn’t made you more confident will just make you even more upset and anxious.

To make matters worse, you let this belief that you’re “supposed” to be having this kind of sex get in the way of relationships you do want. To quote the sage: there’s a million fine looking women in the world, dude. But they don’t all bring you lasagna at work. Someone you click with, who love for their mind and want for their ass is almost always far better for you than “hot but enh”. Those are the ones that you kick yourself over later. It’s only in hindsight that you realize what you gave up… especially when you realize just how rare it is.

Now this doesn’t mean that relationships are the answer either. I have been on both sides of the equation, my dude. I’ve given up potentially great relationships because I wanted to screw around and they weren’t down with that. I’ve also been in relationships for longer than I should have been and missed out on opportunities because of that. But what I can tell you is that, all things being equal, the quality of the connection will always make you happier than quantity of bodies. The better the connection you have with someone, the better the sex tends to be because you’re able to actually connect and communicate. You’re able to really share with each other and find the things that turn you both on.

And besides: the second time around, they let you do the weird stuff.

But for real, BtB: I think your problem is that you think you’re supposed to be one way, when you really aren’t. Again: been there, done that, started the blog. I thought I wanted to be the club guy. Fast forward far too many late nights and way too much wasted money and that’s a big-assed nope. I was trying to swim against the current of my life’s particular river and believe me: that was a lot of time and energy I could’ve been spending elsewhere. I don’t regret it – it’s what brought me to where I am right now, after all – but man it’d have been nice to have learned those lessons a little faster.

Trust the voice of wisdom when I tell you that you’re better off pursuing the women you’re actually attracted to instead of the ones that society tells you that you should want. If you click with slightly older, more accomplished women… well, that’s going to be way less effort than trying to maintain your erection and pretend you give a damn what that 20-something coed has to say.

Now, if you are someone who needs sexual novelty or who has a high sex drive and wants to bang out, then hey, I approve. Rock out with your c

k out dude. But even then, you’d be better off pursuing women you share commonalities with – even if they’re (gasp) in their 30s, instead of nubile 20-somethings. At least then they’d be people you’re genuinely interested in and can have some sex you might actually enjoy. Plus: you’d be surprised at how many women in their 30s and 40s would be down for some no-strings sex with a hot 20-something dude.

Good luck.

DEAR DR. NERDLOVE: First, a little backstory, but I promise I’ll get to the point eventually. I’ve read a lot of your articles these last months. This, combined with reading Brene Brown’s ‘Daring Greatly,’ has been a big help in pushing myself to get out there and make connections – I’m 22, almost 23, and was starting to despair (genuinely lose all hope) of ever meeting someone who I liked that would (miraculously) like me in return. But these two resources gave me the push to try and actively put myself out there – still barely worked, I never would have managed to message her if she hadn’t sent me a like, and it still took me nearly 3 days to screw up my courage – but it changed my life. The last seven months have been some of the happiest in my life. She’s just as nerdy and socially awkward as I am, we share about 90% of the same interests, and it’s great; it is even worth going long distance. She’s a couple years younger than me, and we’re both virgins, and it isn’t technical, either. Hell, she was even my first kiss.

Now, even though I know it’s irrational, I’m having huge anxiety again. Why? She’s hinting that she wants to become physically intimate, which I definitely don’t have anything against. Problem is, I still have almost non-existent self-esteem, much less self-efficacy, where romantic and social issues are concerned. Despite everything I know (and probably also because of it) I’m terrified of being… disappointing.

It’s irrational, I like her and she likes me and so on, but I know in my gut I’ll never forgive myself if I let her down. And in spite of everything I’ve learned (I research basically everything) about different precautions, I’m also terrified at the remotest thought that I might cause her the slightest pain. I want to, but all this conflict in my head is tearing me apart!

If you have any advice for me, please! I need all the help I can get, because I’m exceeding my capacity to work through my issues on my own (again). Anything you say can only help – I reckon I’ve already done about as much damage to my psyche as possible, lol! 

Please help. She’s coming to visit this weekend, and I can only stall so much! 

Thanks,

Stuck In First

DEAR STUCK IN FIRST: I’m going to do you the favor that you need and tell you exactly what to do: DON’T have sex with her.

For real. Take sex off the table. Just accept that it isn’t going to happen this time. Because right now, you’re freaking yourself out over something that’s entirely theoretical and that’s going to make it impossible to actually enjoy her visit. So sex? Not happening. Can’t disappoint her sexually if you don’t actually have sex, yo.

So instead, you’re just going to relax around her. Savor the feeling of being with her. Pay attention to the little things: the warmth radiating from her skin, the scent of her shampoo in her hair, the way she fits up against your side. Be in the moment with no agenda other than just the two of you being present. Don’t worry about performance, being an amazing lover or the risk of disappointing her. Just take each moment and be incredibly present. Let each touch, kiss or caress be it’s own goal and just appreciate how it makes you both feel.

And you know? You’ll probably both be a bit curious. So talk. What does she like, anyway? What turns her on? Cool, here’s what you like and what gets your motor running. And maybe there’s this thing you’ve been interested in but have never done, what about her? Oh, that’s something she wants to try? OK so like this? How does this feel? How does it feel when she does that to you? Ok, lines might start to blur and that resolution that you’re not going to have sex may start to feel a little strained. That’s ok. You’re doing the right thing. Keep that dialogue going – asking, sharing, checking in and just being present. But without expectation – after all, you’ve already let go of the idea that you need to perform for her. So now you’re free for the two of you to talk and share and experiment and see what works for both of you.

Trust me: things will take care of themselves.

Good luck.

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