To build true confidence there are only two things holding you back. Beliefs and lack of experience. If you have negative beliefs and really feel them on an emotional; level then most likely thats gonna stop you from getting confidence. But if you do have positive beliefs but just lack experience then whenever you do something courageous you automatically get confidence. For me I thouight the only way to get out of my negative situation was too just get out of my comfort zone.
Boy was I wrong. No matter what I did I didnt feel like I was getting the right amoubnt of confidence for the things I was doing. Then I started working on my beliefs through some NLP work and realized that my beliefs were whats holding me back. After doing some inner game and belief work I started feeling like I was getting what I deserved. So the things that are holding you back are your beliefs or lack of experience.
First, what id suggest is to just go out experimenting and start small. Approach average woman and just start conversations with them and see if your getting more and more confident. If not then get to work on your beliefs. If you dont know where to turn for your beliefs then, honestly, just quit thinking so much and go out and do it.