DEAR DR. NERDLOVE: I’ll get right to it. I’m 44. A virgin. Never had a girlfriend, haven’t even made out with a girl in 15 years. Admittedly for years I was indifferent and didn’t even try to date, just thought it wasn’t in the cards and for years it was less stressful.

Well, women are like a drug. If you don’t bother with it it’s no big deal. Then you get a taste of it and you want more and go through withdrawal if you don’t get it. Somehow landed a couple dates with a cute girl a few months ago, thought it went great but ended up in the Friend Zone. I’ve only texted her once during the pandemic and no response. I know not to bother trying again, so I don’t show I’m needy. Inside I am, along with insecure and anxious. And obsessive because I don’t have abundance.

I have a fear of rejection after the fact. By that I mean if I asked someone out and they say no, I don’t care. I’m afraid if I actually do meet someone what will happen if they eventually find out I’ve never had a past relationship. I’m anxious if I get her in the bedroom I will come across like an awkward fool and turn her off. I’m worried I’ll be rejected when she finds out I don’t make much money, or live in a dinky basement apartment with no couch. It would be easier if I had a clear direction in my own life, but I have various jobs, and don’t know what I ultimately want to do. That is a problem when dating in my age group, because a woman wondering if I’m husband/father material and what I want out of life is a factor. If it comes up I have no answers.

I simply don’t have much of a social life. My friends are all married homebodies. My only option is going out alone, which makes me self-conscious. What chance would I have if I approached a group of women? They would think I’m pathetic I’m there alone and there would be no chance of establishing attraction. I simply have no one to go out with to lounges or clubs, and I am never invited to any parties to speak of. Advice on dating sites always comes down to saying I should just go out and talk to women everywhere. How is that not creepy? I have no chance of getting a phone number from a woman on the street in the middle of winter, or waiting on line at a grocery store. I just don’t see how that’s possible. I have started trying the apps, but that’s been a dead end so far.

Obviously this all applies to when the world opens up, but how do I retrain my brain from scratch to at least see if I can meet and get in a relationship? And again in terms of the bedroom, I really have no clue what to do. I would like to think natural instincts would take over but who knows. Funny thing is I’m a good talker with great sense of humor, but it has never translated into a relationship/sex. So I’m putting it all out there, what should I do when I have no idea where to start?

Starting From Scratch

DEAR STARTING FROM SCRATCH: Alright, SFS, there’s a lot in here that needs to be addressed, so let’s take it from the top.

To start with, you should be taking a look at the language you’re using. As any writer can tell you: words have power, and the words one uses and the way one chooses to describe things shapes how you see the world. That’s why there’s a world of difference between “police shot a reporter in the eye and blinded her” and “a reporter was struck by a rubber bullet and blinded”.

When you describe women as a drug and “going through withdrawal” when “you don’t get it”… well, it makes for a not-bad single by Roxy Music but it’s a shitty way to view people and it’s going to affect how you interact with people you might be into. The same goes with talking about “ending up in the Friend Zone.” You didn’t end up in the Friend Zone, she just wasn’t interested after a couple of dates and she ghosted you. It’d be nice if ghosting were less of a thing, but it’d also be nice if I had a winning Powerball ticket.

This ties to the bigger issue that you’re having and are going to continue having is that you’ve crafted a narrative out of your anxieties and assumed that it’s the truth without corresponding evidence. The anxieties and worries you have are very common, especially among inexperienced guys, but have very very little relationship to reality. While yes, in a world of billions of people, there are probably folks who would refuse to date someone who had no experience, the odds of encountering someone who actually gives more than half a damn are lower than your odds of getting eaten by a shark. The same goes for her discovering that you’re a virgin or that you live in a basement apartment. These are the things that you feel bad about, being projected out onto the world around you.

(And incidentally: women deal with this too. Plenty of women out there who’re late-bloomers or older virgins get guys who don’t want to date them for fear that being her first would cause her to imprint on them like a gosling.)

You’ve defined the world as having set parameters, parameters based around the areas in your life where you feel deficient, and you’re treating them as being universal without actual evidence. But because you’ve chosen to describe the world in this way, you’re going to react to it that way… and your reactions are going to color how other people react to you. If, for example, you work with the assumption that women aren’t going to like you because you’re inexperienced, you’re going to come into every interaction with them with that on your mind. Not only are you going to be behaving in an almost apologetic way — as if you had to apologize for your existence and lack of experience — but you’re going to have far more negative interpretations of their behavior. You’ll be much quicker to assume that they did X, Y or Z because of your inexperience, when the odds are greater that the problem is in the way you behaved or presented yourself.

Case in point: you’re starting off by assuming that women are looking at you and trying to gauge whether you’re husband/father material… except they aren’t. When women meet you for the first time, they’re not measuring you to see if you fit in the hole marked “husband”, they’re just trying to see if they like you and you like them. And trust me: women are just as nervous and anxious when going on dates as men are. They don’t go on a date assuming that the guy has to prove his worth, they’re going thinking things like”I hope I have a good time” and “I hope I like him” and “I hope he’s not disappointed when he sees me”. The question of whether you might be a good husband or father is gonna come way the hell down the line.

And frankly, if her first criteria is “is this person husband material y/n?” then they’re doing you a favor; they’re not right for you and you’re not right for them and it’s far better to figure that out early on than after you’ve invested in each other. Complaining about that is like complaining that bicycle tires don’t fit on your car’s rims.

Those same self-limiting beliefs are keeping you from doing… well, anything. What would women think if you were at a bar by yourself? Likely nothing at all. The odds that they’d notice or even care are miniscule. While going out with friends makes it easier because hey, you’re out with friends and having a good time, I’ve rolled solo with plenty of success. The people I’ve talked to have almost never asked about where my friends were or even gave a damn if I told them that I was there on my own. I just didn’t treat it like anything weird. “I just felt like going out and having a good time tonight,” was all I needed to say.

(Hell, last time I went out on my own, I ended up making friends with a couple and having an insane adventure in L.A’s underground bar scene.)

Similarly, the advice of going out and talking to people isn’t to roll up on women like you’re Leisure Suit Larry, it’s simply to be social. Are you capable of having a two minute conversation with someone while you’re both waiting in line at Starbucks? What about talking to somebody sitting next to you at the counter at a restaurant or bar? That’s what those interactions look like: simple conversations with people as though they were people and not the Celestials waiting to pass judgement on your worthiness as a man.

All of the things you’re worried about have easy solutions, my dude. You just have to stop treating them as universal, unsolvable problems. The problems you have are internal, and that’s how you solve them. Start by simply focusing on just what it is you want out of life. That doesn’t mean that you need a dream job — just goals and ambitions. Women don’t want a guy who pulls six figure salaries, they want someone who wants more from life than just work and/or lounging in front of the Playstation. You may not have the perfect job, but having things you’re working towards, hobbies and activities that fulfill you, intellectual curiosity and ambition are all desirable traits in a man. You don’t have a penthouse apartment? Dunno if you noticed but most people don’t, especially in this economy.

You don’t have friends to go out with? Well, first of all: you don’t NEED to go to bars or clubs to meet people. You’re just as capable of meeting people at meet-ups, amateur sports leagues, conventions, continuing education courses and so-on. But even so: you can also make new friends… frequently in the exact same places you can meet women that aren’t bars or clubs. Those may be friends who like going to bars or clubs… or they may be friends who just like to hang out, maybe go to the park and throw barbecues.

All things that YOU can do too, by the way.

And as I’ve said many times before: being a virgin doesn’t mean you’re doomed to be a lousy lover. Good sex isn’t in knowing the Swirly-Go-Round or the Rusty Venture or the Transylvanian Twist, it’s in knowing your own body and communicating with your partner.

Like the bodega cashier said to the Buddhist monk after being given a $50 bill: true change must come from within. Focus on the things in your life that you feel are somehow lacking — the lack of focus, the ambition, your lifestyle, and the like — and start fixing those. Start putting in the effort to live a great life, one with ambition, drive, friends and goals. While you’re doing that: simply talk to women. Don’t try to pick them up. Just get to know them as people and realize just how many of the things you’re afraid of are projection and fantasy. The more you feel confident in your life and the more you learn to feel comfortable around women, the more you’ll realize that your anxieties are a paper tiger. They seem fierce and terrible, but they’re utterly fake, a Potemkin village masquerading as the real thing.

You’ve got the power in your hands to transform your life. You just have to be willing to accept that it’s there and actually do it, instead of crafting reasons why you’ve failed before you even started.

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: Brief context: I (28 F) have been in a 2.5 year relationship, 1.25 years of which has now been long distance (12+ hour flight, long distance). Currently coming out of a non-COVID rough patch, newly thrown for a loop.

Ever since I moved away, I have been encouraging him to cultivate friendships because all of his friends are here in the States. In combination with coaxing him into therapy for the past 2 years (which I would say has been moderately successful as he now has 4 consecutive months under his belt after scattershot attempts) I have tried to assist him as best I could in various personal matters (family dynamics, culture shock, opening up emotionally, etc).

While in general very willing to improve, he always found a way to avoid cultivating friendships. He has a mix of friends of both genders from college who he chats with, and we called 2 a day with video calls on weekends as well.

He’s a huge romantic and called me his best friend and that he didn’t need anyone besides me. As the complete opposite of him, I affirmed that I know he loves me and appreciate the sentiment but that all people need someone you can physically meet up with and be in the same time zone with and that no one person can be all things.

We’ve been meeting up for 2-3 weeks every 6 months and we hit a rough patch this January (ironically just before COVID dominated everywhere) While we were working things out (which involved some radio silence for a week or two while we cooled off) he magically gained a “squad” (his words) in February of a college acquaintance who moved to the country he lives in and a high school friend who also moved back.

The college friend is a girl. I’m very chill, but my boyfriend proceeded to tell me multiple times that he thinks she is into him. As he has the social flirting fluency of a statue and had so few friends to start with, I encouraged him to have an awkward conversation or just keep treating her as a friend.

Then he tells me they get drunk together at her place after he helped her run some errands (he is fluent in the local language) and she admits to feelings but she respects what we have.

Given that we were still hashing out our unrelated issues I honestly wondered why he was telling me this. Then he says he feels disconnected from me and our relationship and since he is talking to her for more than an hour everyday about things we used to talk about and meeting up 2-3 times a week, he wanted to know how our relationship is different than a friendship.

I was, needless to say, floored. I asked him if he is no longer in love with me or interested in marriage (aka one of our issues) and he says no. I ask if he has feelings for her and he says he doesn’t think so. I ask if he is attracted to her and he says he can find something attractive about anyone really.

He repeats that everything he used to talk about with me (which was everything under the sun and involved emotional vulnerability a great deal of the time and was apparently a first for him) he now talks about with her. I personally view that as a positive thing as he had a turbulent childhood and consequently great difficulty trusting people enough to converse like that. I’m also not apologetic about not fulfilling his conversational needs because 1) we were in a bad place and needed space 2) he should have people he trusts to talk to and 3) I’m in a COVID epicenter under lockdown—the highlight of my month is finally doing laundry.

Having been a longtime reader, I know you have covered that how men manage emotional intimacy in a relationships other than a romantic partner. Is that related to this or was he never really in love with me—was I just the first person he trusted and decided it was love?

-Lost and Confused

DEAR LOST AND CONFUSED: There’re a couple things going on here, LaC. But before I get into your boyfriend’s situation specifically, I want to talk about something I see a lot in men. Especially men who are a little socially awkward or who don’t have much in the way of social and romantic experience.

One of the things I’ve talked about repeatedly in this column is just how emotionally starved men are. There is a genuine epidemic of loneliness in men, in no small part because we are very bad at growing or maintaining our social circles. We may be good at creating acquaintances, but we’re terrible at making close friends past the ages of 12 or so. It’s not just the inherent difficulty of making new friends after college, but the fact that starting around 11-13, boys are taught that emotional intimacy between men is bad and to be avoided. Any sort of genuine affection or emotional intimacy is equated with sexual or romantic intimacy, which, naturally, is supposed to be reserved for someone you might actually bang.

This ends up creating a cascading effect. First, guys find themselves prohibited from having close friendships with other men except in specific circumstances. But since emotional needs don’t go away just because we think we’re not allowed to have them, men instead look to women for emotional closeness and vulnerability. But since we’re both starved for emotional intimacy and taught that emotional intimacy is de-facto romantic… we also equate that sense of freedom, intimacy and closeness with romantic attraction. As a result… you get a lot of women who think they’re having the same sort of friendship with their guy friends that they have with their girl friends, while guys are thinking that they’re on the road to pound town. This fundamental disconnect frustrates and angers… pretty much everyone really. Women feel like their friendship is being used as a stalking horse for dudes to try to get into their pants and guys feel like women are cruelly teasing them by denying them the sexual intimacy they expect to come with the emotional intimacy. 

This, incidentally, is part of why so many guys find themselves in The Friend Zone; they are so starved for an emotional connection that they round what they’re feeling — often for the first time in years — up to love. It’d be akin to a starving man thinking that the first meal he’s had in weeks is a feast in a three Michelin star restaurant.

Now let’s talk about your boyfriend. It’s actually admirable that he’s done exactly what you’ve been trying to get him to do: he’s gone out and made new friends, opened up emotionally and found himself new friends. That’s awesome!

It’s also why things are a little up in the air at the moment. I think there’re three issues at play here.

First, there’s the fact that, as you said: he apparently has the social fluency of a rock. I suspect that this is part of the problem; he’s experiencing both sexual attraction and emotional intimacy with someone besides you for the first time in a long time. If he’s not used to being friends with someone of his preferred gender (especially if he finds them attractive) it’s not much of a leap for him to feel the same stirrings and think that this is the same as what he has with you.

Second, there’s the fact that she’s been open with the fact that she’s attracted to him. An attractive woman showing interest in someone can be a heady feeling, even if you have no interest in doing anything about it. If it’s something you’re not used to, it can be especially intoxicating. The idea that someone finds you desirable — especially at a time when you were feeling lonely — is exciting and that reflected desire and excitement can feel a lot more than it actually is. There’ve been no few folks out there who’ve gotten caught up in the excitement of someone thinking they were hot and realizing down the line that they were more invested by the other person’s attraction than having any interest of their own.

Third… to put it bluntly, you’re across the globe and she’s right there. The fact that she is attracted to him, he feels this emotional connection with her and she’s physically in the same room with him can be a very potent combination. Add to to the equation that a) you two had just had a pretty major fight and b) she’s got the appeal of novelty and it’s very easy to see him taking all of this and rounding it up to “well this is basically the same thing right?”

It’s possible that yes, you were the first person he trusted and he rounded it up to love. It’s equally possible that he’s so unused to having a close female friend that he assumes that it’s exactly the same as having a girlfriend; the only difference is that he can bang the latter but not the former.

Without knowing the guy… I’m inclined to lean towards the second. I think this is something he’s unused to and doesn’t have the vocabulary to express or even fully understand.

However, I will say that there’s one thing that sets off my Spidey-sense: he mentioned that the two of them get drunk at her place. While it’s certainly possible for that to be entirely innocent — people get drunk with their friends all the time — in his situation specifically, this could be the set-up to an “accident” where one or both of them fail their Wisdom saving throw and end up crossing lines they don’t intend to. I don’t think he’s planning on doing anything he shouldn’t, nor do I think that this is a hook-up in the making. It’s just worth noting that the two of them have created a situation where the odds of a mistake happening are higher than they would be otherwise.

What does this all mean, and what should you do about it? It’s hard to say, honestly. You can’t exactly pound emotional fluency into somebody’s brain. Even having long conversations about various forms of intimacy and relationships doesn’t guarantee he’s going to get it. This is the sort of thing that ultimately folks mostly learn through experience. Like trying to describe the color blue, it’s the sort of thing that you have to actually going through it and realizing how the relationship with a friend is different than the relationship with a committed partner. It can be a frustrating, especially when there’s nothing you can do, but sometimes life is like that.

Honestly, I think the best thing you can do is keep those lines of communication open. Being able to express yourself freely with him and giving him room to express himself will make it easier to keep your connection strong. It’s possible to say “hey, just so you know, I’m feeling a little uncomfortable with this and I’d appreciate some reassurance”  without telling him “hey you’re not allowed to do this.” Plus, being able to talk about these things with each other can help keep the connection strong… and reminds him just why you two fell for each other 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 was a bit of a late bloomer, and have only relatively recently given much thought about relationships and my sex life. Outside of a brief relationship (a few months) out of high-school, I have had much experience. I currently feel that where I am now, I’m not particularly interested in a long-term relationship, but I am open to something casual and even no strings attached hookups.

The problem I have, is that the country I live in has a very conservative attitude about sex and relationships. Most people here consider sex something to happen only within marriage, and people (both men and women, though not equally) are judged very harshly about premarital sex. There also isn’t much of a nightlife here (alcohol is available but highly restricted and expensive). As a result, I feel like it’s absolutely impossible for me to have a casual encounter where I am, even if I were to go out and socialize.

I hope you may have some insight or advice into my predicament. Your articles and videos are great, thanks for the work you do.

Eager But Stuck

DEAR EAGER BUT STUCK: The funny thing about sex: no matter what culture you come from or what laws they may have had about sex and sexuality… sex always wins in the end. People like to get freaky, bang the way they prefer to bang and with the people they prefer to bang out with. Laws restricting pre-marital sex or extramarital sex, laws prohibiting same-sex relationships, even masturbation and sex-toys have never kept people from f

king. It has only either driven it underground or lead to the discovery of some very creative loop-holes.

(Seriously: nobody has ever bought a sex toy for condom application practice, all those “neck massagers” aren’t going on necks and “for novelty use only” has never meant someone didn’t stick their junk in it or shove it inside themselves…)

So the odds are that there are far more people in your country and home town that are down with a little pre-marital action. It’s just a matter of finding them, which is going to involve some detective work on your part. As with folks trying to find the potential partners who’d be right for them,, a lot of what you’re going to need is to start looking for the places where the folks who are most likely to cool with casual sex are likely to hang out — virtually or physically. Dating apps are the most obvious answer. While people, especially women, are less likely to openly advertise that they’re interested in casual hook-ups or no-strings affairs because that’s frequently an invitation to turn their email into the end point of a dick conveyer belt, swipe apps like Tinder are hotbeds of people looking for some strange.

Similarly, you may want to look within social circles, rather than clubs or bars. While yes, a bar or club scene can help facilitate a no-strings hook-up, that’s not the only way, or even the best way. Alcohol may be a social lubricant, but it can also be the lubrication on a slippery slope of bad decisions. A lot of bar or club hook-ups end up being one-night stands because people’s judgement get impaired and they end up deciding to do things that they probably would’ve avoided under the cold light of sobriety.

Plus, there’s the trust and pleasure factor. One of the reasons why women are less likely to indulge in a casual fling is because the risks are high and the odds of the sex being any good are low. This is especially true when it comes to one-night stands and same-night hook-ups. Most men are all but guaranteed to orgasm during sex. Straight and bi women are far less likely… and the likelihood drops even further during a one-night stand. A lot of guys see one-night stands as all about their chance to get off, and simply don’t see the point in trying to bring their a-game to someone they think they’re not likely to see again. That turns a lot of women off the idea of casual sex entirely. Who wants to risk pregnancy, STIs and physical violence for a guy who thinks that monotonously pounding away like a fleshy jackhammer is the ne plus ultra of good f

king?

This is why you’re more likely to find people who’d be open for a fling or a casual arrangement with people who they know and trust… especially if pre-marital sex is taboo. In a restrictive culture, people are more likely to keep similar arrangements in house, as it were. Even when there aren’t explicit laws on the matter, when there’s a lot of societal opprobrium, people are more likely to want to stay on the down low and stick to people they know or trust. Nobody wants to have their vulnerability and openness rewarded by shaming them or insulting them for doing the thing their partner asked for in the first place.

But regardless of where you meet people or how you meet them, you’re going to have to put in the work to be someone they’d be down for hooking up with. It won’t help if you discover the secret underground sex party full of writhing hottness if people think you’re someone who’s going to ruin the party for everyone else. Part of this entails making sure your style and presentation is on point. Part of this entails being somebody that women can trust, someone who is absolutely physically and emotionally safe, who focuses on enthusiastic consent and mutual pleasure and enjoyment. But the biggest and most important part of finding a casual partner is being a great casual partner. One of the single biggest barriers to casual relationships — especially for women — are the number of folks who think that being in a casual relationship means treating your partner casually. Far too many guys tend to think that if they show an ounce of kindness or friendliness to someone they’re only casually seeing, she’ll assume that this is more than it actually is. Not only is that insulting to the people they’re sleeping with, but it ends up being a justification for treating their partner like a living Fleshlight… which is a great way to ensure you’ll never sleep with them or anyone they know ever again.

So do your research and do your work, EBS. Connect with people, make friends and contacts. Be friendly, warm and flirty, but also be honest and up front about what you have to offer, what your limits are and what isn’t on the table for you. Be able to take refusals or rejection with grace and aplomb and acceptance with respect and care.

And if nothing else, when you meet someone who seems like they might be down for something casual, just ask yourself: what would Captain Jack Harkness do?

Good luck.

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