Ask Dr. Nerdlove

Am I Doomed By My Inexperience?

DEAR DR. NERDLOVE: Reading your articles as an inexperienced man is always reassuring, even when things seem pretty bleak. The truth about me isn’t that I’m socially anxious, terribly ugly (I guess?), or too meek. I’m introverted, but much of my pain is due to not actively trying, and an inferiority complex.

I’ve always been down on myself. I’ve thought of myself as a social reject and someone who’s pretty ugly. I can socialize and make friends, but there’s always been a lack of confidence and low self-worth when it comes to dating. I didn’t have a relationship until I was 26. It tormented me for a very, very long time. I was stressed that my time was running out, bitter that I had wasted my youth. It took me so long to sort out my life and actively try because I was depressed, doing poorly in college, and went through cancer treatment at 22/23. After enduring chemotherapy, I was convinced nothing would ever go right for me. I’m grateful to be in remission, but I’m still a resentful, melancholic and bitter person.

I feel old, like time has passed me by. I wish I hadn’t lost my teens and early 20s, so I feel the pressure to play “catch up.”

At 26, I met a girl who I felt a good connection with. She was going through a hearing (abusive ex), and had also been sexually assaulted. She has had her own issues with depression and anxiety. She would self-harm. I could tell she was deeply in love with me. There was mental connection, but she was also really physically attracted to me. She even introduced me to her parents right off the bat, which was surprising. Our first three months were nice. According to her, I was a good partner, attentive, supportive, intelligent/intellectual, and “made her feel safe.” She had her own insecurities about her body and looks.

I took some time before I started staying nights, because I wanted to respect her boundaries and not push for sex. I made her orgasm pretty easily through oral sex, using my fingers. I was good at foreplay, and a decent kisser. I would make her cum consistently when we were intimate. She would usually initiate, and seemed genuinely into it. I still feel like I fell flat on my face though. This is because I had a few instances of performance anxiety and premature ejaculation. I put such a burden on myself to perform and get a girlfriend that I was super tense. We didn’t ever get a chance to build further physical chemistry and have intercourse. I avoided it, under the assumption that we’d get time to work on things later. I didn’t really enjoy sex, it was more about getting her off. She never ridiculed me, seemed angry or disappointed. She was understanding. Unfortunately, it turned long distance over the summer and fell apart. She broke up with me, saying she didn’t feel enough to keep things going, and she had wanted more closeness.

I feel pathetic that I wasn’t able to perform for a woman who really liked me. I’m not sure I was interested in a LTR, or immensely physically attracted to her. I felt guilty about this. I feared I was “bad in bed” but she had said I wasn’t. I guess I was attuned to her needs. I asked her if she left me because of the anxiety, but she denied that too. She had said that I made her cum faster than her previous partner (the abusive ex). My insecurities are back with a vengeance. I still feel like an inexperienced loser, and certainly still feel like I deserve the label “virgin” (there was penetration but I wasn’t fully erect). I wish I wasn’t so burdened with past insecurities.

I can’t quite feel proud of myself for being a decent boyfriend. I feel like I failed at a fundamental aspect of a relationship. The breakup is not what I’m stressing about Doc. I’m just concerned that I’m an impotent, spineless wimp who squandered the only opportunity I’ve ever had. Kissing three women, and intimacy with one woman doesn’t seem very impressive for a guy who’s now 27. I see many sex columnists ridicule older virgins, but I don’t think there’s anything wrong with me physically.

My question is simple. How do I stop beating myself up? How can I force myself to see that this was a huge step forward for me. It’s in the right direction, at least. I went from thinking I’d never have a partner until my 30s, to having a really loving partner.

Problem is, my sex drive is pretty low, and I’m constantly ruminating on what I did wrong.

I’m more devastated than I probably should be, given the circumstances.

How do I keep going? I feel like this is a sign that I’m not cut out for having a good dating and sex life. I still can’t accept that anyone would actually like me.

-Haunted by the Past

DEAR HAUNTED BY THE PAST: There’s a lot to unpack here HBTP, but I want to lead with this: a lot of your issues are self-inflicted. Don’t get me wrong, I’m not saying that they’re not real or that they’re not legitimate. But a lot of the problems you’re having have less to do with the world around you and the way that you’re looking at it.

I mean, we can start with the way you describe yourself: as a social reject, who’s ugly and has no inherent self-worth. You’ve convinced yourself that nothing could possibly work out for you. And if I can be perfectly blunt… you’re not wrong. Rather: you’re not wrong because you’re going to see everything that way.

See, attitude is destiny, HBTP. The guy who’s convinced that he’s ugly and nobody could love him is correct. Not because he actually is ugly and unbangable but because he can’t conceive of the possibility that someone would find him attractive.

This means that even if someone were to approach him and flirt with him, he’d dismiss the possibility that she was legitimately interested. Oh sure, she was talking to him. She may have even seemed flirty. But clearly she was just being friendly. Or he was misreading things. Or there would be any number of perfectly reasonable explanations for what was going on that had nothing to do with her actually being interested in him.

But the opposite is equally true: the guy who’s confident in himself and his attractiveness is more likely to find women who are interested in him. Not because confidence is inherently sexy – though that certainly doesn’t hurt – but because he’s actually looking for it. He’s more likely to pick up on the signs of her interest because he believes that they’ll be there. And if he’s wrong? Then he’ll chalk it up to being a a learning experience and move on. To him, setbacks, while inconvenient, are temporary. They’re something to be overcome with time and effort.

I mean, let’s look at the example you give, HBTP. Not your ex – more on her in a moment – but on the fact that, holy hopping sheep s

t, you survived cancer. I get that chemo is rough, I’ve had far too many friends who’ve gone through it, but come on! You think thinks can’t go right for you? Sweet Jeebus my dude, you beat the plague of the 21st century! That alone is should be a sign that you have the power to grab life by the hair and start dictating terms. Yeah, being dumped is a shame but God HIMSELF couldn’t put you down.

So much of what’s happening with you is because of how you’re seeing the world. Your ex, for example. You made her almost mythical in her importance. It’s no wonder you were having performance issues; you put so much pressure on yourself that you couldn’t perform. Dicks are divas; there are plenty of times when they’ll refuse to work if things aren’t exactly perfect. Usually at moments when you desperately need them to perform. You put so much pressure on yourself by treating both your virginity and your girlfriend as the end-all, be-all of your existence that I’m less surprised that you had performance issues and more surprised by the fact that your junk didn’t just recoil all the way into your body cavity and call it a day.

And if I’m perfectly honest, HBTP, I’m not terribly surprised that your relationship didn’t last. While I’m sure your ex was a great person, neither of you were really in a place where you could be dating… and she wasn’t going to be a good match for you, regardless. It’s not that you failed at being a boyfriend or that you couldn’t accomplish some critical aspect of being in a relationship, it’s that you were in a relationship that wasn’t going to last, regardless of what you did.

More to the point, however, is that you’re treating it as a definitional experience, when it was nothing of the sort. It wasn’t your defining relationship, it was just a relationship. It wasn’t your forever, but most won’t be. Instead of treating this as a mark of failure on your part, the thing to do is to learn from it for the next time. Because there will be a next time.

There’s nothing wrong with you, HBTP, either as a partner or a lover. While I wouldn’t say you’re a virgin, the truth is, whether you’re a virgin or not doesn’t mean a damn thing. There’s no qualitative difference between someone who’s had penetrative sex and who hasn’t; it just means one has had an experience the other hasn’t. As I’m fond of saying: sex isn’t a test of your worth and women aren’t Mjolnir. Women don’t have “Whomsoever should part these thighs, should they be worthy, will gain the power of Score” embroidered on their underwear.

People have sex for reasons that often have nothing to do with the person they’re having it with. Sometimes they want validation. Other times they’re trying to prove something or get back at someone else. Still other times they’re doing it out of a sense of obligation. And of course, there’re times when they have an itch that they need to be scratched and the other person is the closest acceptable warm body.

The truth is, HBTP: you’re doing amazingly well. You’ve made a lot of progress, got some experience under your belt and – oh yeah – you beat cancer. Your problems are strictly in how you’re seeing yourself and the world… and the good news is that you can change that.

You don’t need to talk to me, you need to be talking with a therapist, my dude. The best thing you can do for yourself right now is to find a counselor to help you work through this lack of self-esteem you’re dealing with. It may take you a couple times to find a counselor and a therapy that works for you. That’s fine. But the sooner you get started, the more you’ll realize that you may not have a lot, but you can turn it into more than it seems.

Don’t let your jerk-brain define you, HBTP. Your experience – or lack thereof – isn’t something to be ashamed of, nor does it mean that you’re deficient or worth less. It’s just a lack of experience; it’s neutral in and of itself. Spend time working on getting yourself in good working order and in a place where you can put yourself out there with more confidence. Your experience will take care of itself. 

You’ve got this.

Good luck.

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