At the moment, this is my situation. Single, attractive guy who gets attention from ladies. As soon as they show interest i back off, and don't initiate, then when things don't go my way i over analyze shit and start thinking why in the world am I not actually actively pursuing these girls, instead of being a pussy and just waiting for a woman to fall on my dick.

TLDR; - have options, but do not pursure.
- find myself sitting there after craving a woman but get to that same point and pull back a few steps.

PS this is with chicks that area actually present in my life, not for chicks that i find when im out.

I know theres something wrong with my mindset, that's why im asking. More im trying to find out WHY i am doing this from a psychological POV, and then to overcome it.

You're delusional if you think looks alone matter. Women will make it easier for a guy to open them if they're interested but if you fail to take the ball they figure you aren't interested and move on to a guy who will reciprocate. I had the same issue when I was younger, and then I grew a pair.