Comfortable where u can be yourself unforgiveningly. Comfortable to the point that u know what to expect from him. To the point that you aren't trying to leave an impression on him. Here's the scoop: I been talkin and watching this chick for about 6-9 months And I've come on to her extremly slowly. First the eye contact, then the confident not looking away eye contact, then the waving...we have had a few in depth convo's eventually and we learned a lil bit about each other both times and we both asked each other questions and shyt. But I have allways been impressed how I can keep a woman's attention when I know she isn't completely comfortable around me. I mean I know a woman isn't comfortable around a guy until she sees how he handles his anger towards her and puts him through some tests. So I know they not comfortable yet. I jus wanna know how long do you give a guy to get comfortable with?