2) Soon. The accolades, I mean. First, I will offer one friendly and helpful suggestion. Catastrophizing of the causal variety involves extrapolating calamitous results from a seemingly insignificant cause. The comment from your friend is just such a cause. You err, however, when you indicate that you feel women want nothing to do with you because of that comment and the fact that you have made nothing of your life. You should be entertaining the possibility that you have led a totally and irredeemably failed life only because of that comment. The important point, I realize, is that no woman will ever find you attractive, but I nevertheless feel that the chain of reasoning should be sound.
3) One other thing concerns me: you shouldn't need a casual comment from a friend to feel small. You should be able to feel small at the slightest provocation, or at no provocation at all. You should be able to conclude that you're small on the basis of a comment your friend makes on a topic that seems to have nothing to do with you whatsoever.
4) Don't feel discouraged by my constructive criticism. You are well ahead of where most people are already. You feel small when probably you shouldn't; you allow this probably unfounded feeling to prevent you from asserting yourself with women for three decades. You are well on your way already. Just spend more time considering your lonely future and friendless dotage and in no time at all, you'll really be catastrophizing!