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Hey everyone, I am also reading "The Game", and for someone that doesn't like to read anything other than a magazine, it is an enjoyable read.
My sticking point is being frightened to approach a set, and knowing if a girl is single or not before the opener.
Unfortunately, to get good at all of this, you will have to read a bit. You need to learn some theories - but then you also need to make sure you put them into practice.
As for your sticking points:
1) read up on approach anxiety. We all get it. Even the masters get it. We just overcome it
2) It doesn't matter. Open her anyway.