Been approaching a lot, but...

        I still seem very nervous, skittish, and unconfident. I'm talking to them and all of that. Been through a lot of rejection. A LOT. Anyways... I've been feeling pretty down on my self lately, cause I've had some success, but not as much as I'd like, yet I still go out and do it. I'm kinda starting to think that maybe because I approach and talk, but don't push myself out of my comfort zone enough as I try to move forward. Like I feel almost comfortable approaching and talking, but not going any further than that. Am I right in my assumption? Will the confidence that I'm looking for come from pushing myself even further out of the comfort zone? 
       I was always told it's just a numbers game and to go out and keep doing it and eventually I'd figure it out. However, I feel confident I can hold a conversation, but beyond that? No way. Also, why is it that some people with practice, seem to be so observant of how other people react, when they say something, but I'm still pretty oblivious? Like whats up with that?