If you lived close to the west-coast, I could take you under my wing for a weekend and show you the ropes...
There are a few things I remind myself of, before I go to encounters with Females:
1) They are stupid as shit, and only want to hear what they want to hear... so feed them some bullshit. They want to know that you are passionate about something, that you care about shit like a hurt cat on the side of the road..
2) DO NOT put them on a pedestal... Actually, the less you can "seem to care" about them at the present time, and the more you can seem to "just be passing the time by talking to you" the more interested they will be.
Annnnnd... This guy nailed it. Confidence is NOT about being good-looking, or rich or being 'hung'. It's about being who you are, and being perfectly comfortable in that skin, with all the strengths you possess as well as flaws. Trust me, EVERYONE has flaws and insecurities... Life is about adapting and dealing with them appropriately.