How to get past surface conversation?

I have a hard time getting past surface conversation, and flirting with a woman the correct way. The biggest thing is I have no idea of where to start, or even doing it without coming off as awkward. Secondly, I tend to be oblivious to whether a woman really likes me, vs just wanting to be friends. I just tend to think that most women are being friendly, and so I don't make a move. This on top of my inability to really direct the conversation and steer things to a deeper conversation. Even with my lack of "Game," I try to make things happen, but the harder I try the more I seem to fail. I need some serious help.
How to get past surface conversation?
Post Opinion