Hello Doc,

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

[Read more…]