At what point did pick up start becoming automatic for you?

I'm at a place where I'm comfortable just going up to a chick and saying what's up. Problem is my game skills are dripping over into all interactions I have with girls, and so I'm gaming without really even trying to.

If I go out to approach, then I go for closes. But, if I'm just talking to the chick behind the register and she's acting invested or what not, I tend to not ask for numbers and stuff and afterward think "Wait I probably could have asked to go for a drink" etc.

So yeah. When does pickup become so automatic that you do it in all contexts? Or is it just a thing that needs more practice.