So 40/m, charismatic, experienced, and very good at reading people in general.

So this is more advice for younger guys, but I still trip up on it.

2 types of initial random introductions to women you are attracted to, 1 is cold, 1 is warm and possibly into you right off the bat. If you don't ask the one that is on the warm category after the first 1-3 times of bumping into her, it's over, she thinks you are a pussy for not asking her out. Move on, don't pursue this road anymore. Opportunity passed you by.

That one that starts cold, and eventually shows warmth after like the 3rd or 4th bumping into. It's still on. And focus on that.

Assuming these are both scenarios where you are really really attracted to each one.