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The whole calibration thing definitely fits my experience. I think you just have to build up some comfort with being in a sexual situation.
Regardless of fault, it's not rational to drag your parents or your upbringing into the situation at this point. They may have been the root cause of the problem, but they can do nothing to fix it for you now. However, it IS within your power to do that.
This can help, but I think it's just confidence in general that will help you in social situations. Fake it until you make it (become it). Your self image is largely impacted by your behavior even if the behavior is forced (look up some of the research done by Amy Cuddy, it's interesting stuff). As for the “Weird Tells,” remember that what's going on in your head is a mystery to others. Someone with only part of the information is going to assume the worst. You see some attractive woman you'd like to talk to, but you don't know what to say or how to break the ice. So you don't say anything and now you feel uncomfortable. She sees this uncomfortable, anxious looking dude who seems to be paying way too much attention to her... Danger Will Robinson! Danger! I think it's better to be awkward and open than awkward and withdrawn. The first makes you seem less of a threat and the second lets the imagination go crazy. Either case exposes you to a lot of potential negative feedback, so just accept that as a given and drive on.
I'd like to say something along the lines of “you should try with women that you may actually be able to form a relationship with.” To be honest though, If I were in your shoes, I know I'd be looking pretty seriously at Nevada right about now.
Finally, there's no dark side here, and it's not irrational. Thinking that you shouldn't have, shouldn't want, or don't deserve what 7 billion other people have and want is pretty irrational. Make the map fit the territory. MrMind is right, you don't need to rationalize doing something that's perfectly rational to begin with.
In any case, good luck with your sex life (and good luck with that novel too).
Psychotherapist Albert Ellis writes in one of his autobiographical recollections that he had tremendous anxiety as a young man about talking to women. So, anticipating the kinds of advice given by today's self-styled dating coaches and pickup artists, he forced himself to try to start conversations with 100 consecutive women he didn't know in public pla... (read more)