@PatientChaos,
I think some day you will find some lady and totally forget about all this crap you think is important. Because this person will cause you to totally forget yourself. All the rest follows - being friends, being 100% yourself, worry over social norms, over time.
Believe me, this lady will bring out the spontaneous person you don't even know is there. Self-analysis will only be a memory.
At least, this is the way it happens in those old movies.