I'm an athlete. So I guess the whole confidence thing comes very naturally to me. Unfortunately, I train... a lot. I have effectively pulled myself out of the main hot spots (clubs, bars, etc). 6 am workouts don't really work so well on a few hours of sleep. I love to bust peoples' balls and therefore am construed as an a'hole. I have no problem starting a conversation and maintaining it (building attraction, flirting, that sort of thing). My problem lies in the fact that once I get to a certain point in the conversation... the do or die moment... I either choke or fail to recognize the need to take the interaction to the next level. Everything feels great until it comes time to set up the next meeting or grabbing a number or even more. Maybe I'm just over-analyzing this and just need to say F it and go for it. But I find myself stuck in a rut.

Any suggestions?