Your issue is simply one thing - inexperience.

The only reason to ever be "up in your head" and over-thinking situations is because either

a) you don't know how to control them or
b) you're worried about how they'll pan out.

Firstly, you need to realise that life is a ride. You just get on, hold tight and go with it. There's not really a lot of point worrying about it, because it's going to go where it wants to go, so you might as well just enjoy it.
What I mean by this, is that you're over-thinking situations because you're probably worried about how they're going to pan out, rather than adopting a "what happens, happens" attitude.

It's only when you really let go of the worrying that you can climb out of your own brain.

And by the sounds of things, you don't need to worry too much with the ladies. I guarantee that there are some good PUA's on here that haven't achieved 14 SNL's. You obviously have something that comes across naturally when you're the "life of the party"... try to find what that is and run with it.