Ask Dr. Nerdlove by Harris O'Malley

How Do I Overcome Being a 40-Year Old Virgin?

DEAR DR. NERDLOVE: I’m looking for advice because although I’m not 40 years old, I will be next year and I’m dealing with a problem I’ve been avoiding most of my life and I’m starting to realize that if I don’t address it now I will be alone forever.

The actual status of being a virgin doesn’t bother me so much as not being able to get started. I’ve somehow gone 39 years on this planet not being able to form a single relationship with another woman. I’ve never been on a date in my life, I’ve faced rejection all my life and sometime in my early 30’s, I just stopped. I wish I could adhere to the “Never give up” philosophy but the truth is that after a lifetime of failures and not a single success to latch onto, I don’t know any other way and I just stopped. I’m tired of being rejected, of being unwanted, dating and relationships became something other people did and I need not concern myself with it.

Now as I’m approaching my 40’s I’m facing the problem of loneliness and not being able to take action when I think I might actually have a shot with someone.

I’ve been crushing hard on a female friend and I don’t know how to handle it. She confides in me, she inspires me and I’m fairly certain she wants me to make a move on her but I just can’t. I’m quiet and mostly keep to myself but she approaches me and even offers to drive me home sometimes and isn’t repulsed if I ask for a hug. I’m confident at least that she likes me as a friend but I’m paralyzed with doubt and fear. I’ve told myself for 2 years this is just some infatuation, I’m crushing on a woman because someone finally started giving me attention and is being friendly and I’m being ridiculous. I tried to wait it out and let the feelings die like these intense feelings usually do, but this isn’t going away and she opens up more and more about her struggles to connect with people and start a relationship due to only being in 1 LTR in her life, if only she knew……

The more I think about it, the more I convince myself to just say something and ask her out or tell her how I feel, the more I realize that I’m just scared. I’m scared of rejection, I’m scared of her getting a boyfriend and yet would feel relief if that happened. But mostly, I think I’m scared she will say yes. Then I will have to spend time with someone and it’s all uncharted territory. I’ve never dated before at all. I went to some bars and clubs in my early 20s with friends and it was among the worst experiences in my life. I’m not social and she is among the few friends I have. I don’t know where to go, what to say, what to wear, what to do, and most of all, just being vulnerable and opening up to someone is terrifying. The anxiety is overwhelming and I find the best recourse is just to avoid her until I’ve cooled down and I’m almost certain if she has feelings for me she must feel awful if I’m never acting on them.

So yeah, whatever advice you can give, I’d love to hear it. All I know is that I have to do something soon because if I don’t, nothing will ever change.

Untouched at 40

DEAR UNTOUCHED AT 40: I suspect the biggest issue you have is one of deservedness, Ua40. A lot of folks, especially late bloomers like yourself, tend to have a hard time in believing that they’re someone who deserves a relationship. The logic — such as it is — tends to be an assumption that if they were worthy of a woman’s time, attention and affection, it would’ve happened by now. Since it hasn’t… well, it must be a sign that there’s something wrong with them.

In reality though, it’s nothing of the sort. More often than not, the thing that holds people back is fear. Not just fear of rejection — which feels obvious — but also fear of success. It sounds absurd; why would someone be afraid of getting what they want? But the thing is: as long as something is only a fantasy or only potential, then you can’t screw it up. A fantasy can be as perfect as you want it to be. Potential means that it could be EVERYTHING and ANYTHING; making it real means that you might make mistakes and have it all fall apart on you.

This is in no small part why some guys end up with crushes on people that either they never ask out on a date or who they know to be unavailable; it’s easier to stick with the known, even when it’s painful, than to try to live up to your fantasies or ambitions.

At the same time, that lack of deservedness can cause you to end up with crushes on people for the wrong reasons. When you feel like nobody could possibly like you or that you’re not “worthy” of love, sex or relationships, it’s incredibly easy to latch onto anyone who shows you a little affection or interest. It becomes almost a recipe for heartbreak because you crave something so badly that the hint of it makes you overlook issues like basic compatibility or mistake platonic affection for romantic affection.

And y’know, I get it, especially the sense of knowing nothing but rejection. That can be incredibly disheartening. And while my general philosophy of rejection is that many — if not most — of the time, rejection has nothing to do with you as a person, sometimes that rejection is a sign that it’s time to do things differently. If you’ve been approaching meeting women and dating the same way and getting the same results… well, sometimes that means you have to take a look at your approach, at all the commonalities and decide to make changes.

Now for you, part of what I would suggest would be to find a counselor or therapist. The fear and anxiety you have is the sort of thing that’s best handled by talking things out with a trained professional, not just a loudmouth with an advice column. But another part of what I would suggest is being willing to go back to first principles and work on not just yourself but your perception of yourself. Who you are as a person doesn’t necessarily need to change, but how you see yourself does. Many times, the reason why guys struggle with dating isn’t because they lack the skill or the courage to date but because they don’t let themselves do what they’re truly capable of.

Part of what people think works about things like pick-up artists or The Red Pill or other systems that teach you how to date and meet women isn’t inherent to the system. It’s not that, for example, Mystery’s advice to dress weird was making people more attractive or that using pre-scripted material made you a more interesting person. What it was almost always doing was forcing you out of your comfort zone and into doing things that you might never otherwise do. Peacocking didn’t make you more attractive, it forced you to think differently about how you dress and to try things that would otherwise be “out of character” for you. Canned material didn’t substitute for a personality, it just gave you the feeling that you could talk to women. Even bulls

t ideas like negging or attitudes about “being alpha” were functionally about getting you to behave differently than you would otherwise.

In a very real way, a lot of pick-up et. al. was the sociological equivalent of Dumbo’s magic feather; it didn’t actually work, it just gave you permission to do things differently and finally discover your true capabilities.

Now here’s the thing: feeling like you have that permission and those capabilities will actually ease your anxiety. Feeling capable, feeling like you have the capacity and ability to succeed gives you a sense of control and agency, which in turn, helps give you a sense of certainty. Part of why you’re so anxious around your crush is because of the ambiguity of the situation; she’s both potential love and potential rejection. Being unable to resolve that sense of “what if” is what’s preying on your mind and on your calm. Getting an answer one way or another — even if it’s a “no” — would end the ambiguity and chaos and give you certainty. A “no, thank you” wouldn’t be the result you would hope for… but it would mean that you would have an answer and you’d be able to move forward.

And honestly, the longer you let situations like this go on, the more anxiety-producing they become. The more time goes by, the more you are invested in the outcome, which means that you’re also making yourself more afraid of a potential “no”.  And now you’re stuck between the fear of success, the fear of rejection and the anxiety of the uncertainty between the two.

So while I strongly suggest that you find a counselor to talk out some of your issues, I think it’s also time to start resolving to act out of character and force yourself out of your comfort zone, so you can finally unlock your true potential.

Part of that would be to take inventory and ask yourself: in an ideal world, what would you be like? How would you act, how would you dress, how would you feel about yourself? Then, as you list these qualities, start to brainstorm ways that you can incorporate them into your life now, instead of waiting for the day when you’re “allowed” to feel, dress or act that way. The more you work to manifest your ideal self now, the more you begin the transformation that will help you change your life for the better.

Another, and possibly more crucial part of making that change will be to internalize one of the lessons that Carrie Fisher left us with: “be afraid… but do it anyway”. It’s ok to be scared or to be afraid of rejection. But the truth of the matter is that the fear of rejection is more painful and more debilitating than the rejection itself. Risking rejection right away lessens the impact it has on you because you haven’t given it time to build and build until it becomes a giant monolithic entity that always lurks in the back of your mind.

And when it has already become this monster in your life? Then the key is to finally face it and get your resolution, so that the ambiguity doesn’t prey upon you the way that it does now. Even being told “no” is better than letting the fear build. While being rejected may hurt, getting that no and facing that pain will do two things.

First: you’ll realize that rejection may suck, but it won’t kill you. You WILL survive it.

Second: by getting rejected, you’ll finally be able to start to heal and move forward.

Resolving that ambiguity will mean that you won’t feel as anxious around your friend because you will finally have an answer. And if that answer is “no”, then you’ll finally be able to heal and move forward with your head held high because you had the guts to do the thing that terrified you. There is honor in that, and you will know more of what you’re truly capable of accomplishing.

That’s why asking your friend out on a date would be a start to transforming yourself into the man you can be. Tell her this:  “Hey, I really enjoy hanging out with you and talking with you and I love our friendship. But I’d also like to take you out on an actual date and see if there’s something more there. If you’re not interested, it’s totally cool to say so; I’m just as happy being your friend.”

You will stammer. You’ll feel your heart pound. But just by asking her, you will have started the process that will transform you. Simply asking the question — a seemingly tiny gesture — is your first step towards a better life. You will have proven that you can do things differently and challenged your limitations. Whether the answer is yes or no, you will have forced yourself outside of your self-imposed limits and put yourself on the path to make your life better. Because you’re right: you need to do things differently, or nothing will ever change.

And even if you crash and burn… well, the phoenix has to burn before it can soar as its true self.

You are untapped potential, Ua40. You are braver than you give yourself credit for, you’re stronger than you know and you’re capable of far more than you’ve ever believed. You just have to reach for it.

It’s time to let go of your earthly tethers and fly.

You can win if you dare.

Good luck.

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