Any advice on getting in the right headspace with being direct with women?

Been reading a lot of "Mode One" and listening to Patrice ONeal's stuff and both are big on being honest with girls and telling them what's on your mind.

I've done a bit of that with girls and so far I've had positive results.

The problem is...I still hesitate telling girls how I really feel all the time. I sometimes talk to them too indirect which I want to change.

If it was up to me I would hit up half the girls on my phone and ask "when we fuckin?"

...but I feel like I'm missing something.

When do you know when to go direct on them or when to play it cool?

P.S: This is more for after you already have their number and whatever...not so much in the approach.