I think you should review the basics first before getting into the specifics of a certain seduction
http://www.jbspencer.com/djb/ (The Don Juan Bible)
http://roissy.wordpress.com/the-sixteen ... s-of-poon/ (Roissy's the 16 commandments)
And also read The Game by Neil Strauss and The Art of Seduction by Robert Greene.
As per this exact situation, you're over analyzing it. Never think. Thinking is for women. Men are creatures of audacity, of action. Just DO. The reason why most natural Alphas tend to be dumber is because they never have time to think to themselves; "what do I say? Do I look stupid? Does she like me?" They Just DO.