Good post.Sounds like oneitis. Sort of like approach anxiety in a tiny village. Fear of rejection because if the escalation isn't welcomed you could lose a very rare mating opportunity and social proof, then you're toast.
Personally I find it helps shortcut the brain and add a little abundance feeling even to passively see a lot of hot girls around. So if you go walk the bar strip at night even without opening, you'll internalize there are semi attainable options around.
Outside of the individual interaction ramping re James above you may also need to simply increase exposure a lot. Also the reference experiences of a kiss being received well, or calibration lessons from it not going well.
"Repetition is the father of learning. Repetition is the father of learning." - Lil Wayne
Edit corrected quote
Approach anxiety generally means when someone lacks enough positive reference experiences and is thinking about outcomes. Its even tougher when someone also has little to no experience with women.
One simply needs to practice approaching over and over again and practice self amusing the whole thing which is of course easier said than done. Caring too much about what may happen is another issue. Need to stop thinking. Just go in and turn it into a fun game. Find things that make you laugh. Find something funny about the interaction and be positive after each approach. In between approaches is just as important as the actual approach.
Just stop thinking. Be more in the moment. Make yourself laugh.

