I'm finding it easy to open on women. From my reading, I see that its better to discuss interests in person like on a date. This confuses me a bit, leaves me wondering how much in depth do I need to go with the chick to Number Close online or date close through phone? Do I just gauge this myself, or is there some other way to progress the conversation to build comfort or attraction. I'm thinking someway to be cocky + funny would work, but NEGing online seems to backfire quite often for me.

What do you guys think?