It really does seem that you are more worried about using women and dating as a way to prove yourself to family, your frat, society at large , and above all to yourself. Try to approach it more from an angle of it being something you want to do just because you want to, not you want to because________, or you want to so________. It sounds like you are in a world where you are surrounded by people who treat women as objects and you don't completely*
think of them that way so you are confused by the mixed messages you feel you are receiving from society vs. from yourself. As you go through life over the coming weeks and months, try to just realize when you get a clear signal from yourself of what it is exactly that you
want, free of the pressure of outside influence. Recognize that I'm not saying you have to be free of outside influence for this to happen, because that influence is not likely to go away any time soon or....well, ever. But just to realize what it is that you
want, not what you want in order to appear a certain way to others or to live up to their standards for you. Start the process of learning to be your own person and living for yourself.
*I say completely because I believe your heart is in the right place, and the thing I think you are doing that I'm about to share comes from a place of not realizing. However when you mention things like never getting in trouble, coming from money, etc. Those things don't mean
anything. It's like there is an unconscious dialogue in your head telling you that because you have money,and never made any trouble, that women should just like you no matter what. It is like a subtle attempt at exchanging money and/or good behavior for approval, but women are people and they respond to people, not money, or obligatory good behavior. (note I'm not suggesting being good is bad, just that you can't expect people to love just because you are good, or rich, or a hard worker, or any number of other things that people often use as a cover up for the parts of them selves they don't like, or fill a void they feel within.)
And finally I'm going to suggest seeing a competent therapist/counselor of some kind could be a good idea for you. Maybe someone who specifically knows how to root out and correct faulty thinking and not just someone who wants to talk things out ad nauseum and blame it all on your childhood but someone with a results oriented approach. Be sure and screen for that if/when you pursue that option.