i didnt read any of the other replies so as to avoid bias/not get distracted
in short, i think that the root cause of your depression is a subconscious realization that all your life, you were doing things in order to validate yourself and pump up your self esteem, rather than because you really wanted to do those things
we all tell ourselves stories so as to cope with our lives/reality. it seems to me that your self esteem is caught up in you somehow living up to a script, where you as the main character have to be financially successful, make lots of money, have hot girlfriends, be the party guy etc like you used to be, when really, deep down, that isnt what you want
in some of your pickup reports i got the feeling that you were trying REALLY HARD to do something (get some girl sexually) when really, what you needed was to connect with another human being, and have some joy in a dynamic where you could just chill out with someone not too different from you and have a nice experience
a nice way to feel out what you really want is to ask yourself, - if everything was a given, what would i do, and how would i act? if it was a given that you could pick up xyz girl, what would you do, and how would you act? if it was a given that you could have xyz job/respect from parents/peers/{insert thing here}, what would you do, and how would you act?
you can have some really nice insights after you take validation seeking and approval seeking behaviour out of the equation