I only get in depth with my best friend who I've known forever. He's trustworthy so we go pretty detailed with it when we talk sometimes. Talking about how the relationship is going, what's going wrong or what she did that was so adorable, how the sex was, what we wish our chicks would do, etc.
Not all guys do it, and on average, not nearly as detailed as women seem to get during their little "girltalk" sessions. Seriously, am I the only one who sees the double standard here? A guy says something and girls get so irritated, call guys chauvinists, pigs, or whatever, but bet your ass half these same girls who complain go into some crazy shit during "girltalk", and 35%-40% out of the other 50% who don't, know damned well what's said yet turn a blind eye, and still call men out.
I don't always tell. Actually I tend not to tell at all unless I am pressured by the person I'm seeing.
My friends are very good at ruining relationships. Good people that make good friends, the most of them, but my private life needs to be kept separate as much as possible. I don't even tell my "best friend" when I've slept with a woman. The only time anything gets announced is if I'm actually dating somebody.