Ask Dr. Nerdlove by Harris O'Malley

I’m A 40-Year Old Virgin. How Do I Learn To Finally Start Dating?

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.

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