> On the other hand, my therapist tells me ...
Ah, now I understand. You had self-esteem issues arising from allowing yourself to be defined by random women's tastes, and you now have the additional burden of allowing yourself to be defined by the random tastes of a therapist.
Let me tell you something. You will become self-confident when you decide to define yourself -- and not before.
You're going through something that many, many people have gone through -- trying to secure validation from other people. One day you will wake up and realize that securing validation from others is like securing happiness by shopping.
By a process of natural selection, nature has made you the way you are. There has never been anyone like you, and there never will be again. Your purpose is to live your life as yourself, not as some imaginary person defined by others.
Evolution works. Natural selection works -- but only if people don't all try to be copies of the same "ideal" person.
> I just can't seem to hack this whole sex thing.
What's to hack? The "whole sex thing" gives too much power to other people. Marketers and commercial interests want you to believe they can sell you success, and therapists are in the same line of work. It's just a big scam -- the trick is to figure that out before you die of old age, still trying to catch the brass ring.
And guess what? If you stop trying so hard, if you come to realize the "whole sex thing" is completely ridiculous and stop giving it any energy, women will suddenly and inexplicably flock to you like moths to a candle.
I know this from personal experience.