You are right I think my main problem is that I try to play it safe and look for a way to get flirtly. I find this is best done as you said being in the moment and the have fun not giving a fuck attitude which will then get her to open up instead of riding on the boring non chemistry building questions. I think this comes from a lack of experience on my part as well as trying to much to not say anything that would stir a negative reaction which may come from an insecurity/lack of confidence. I find myself knowing what to do but not being able to execute and I wonder if that is worse than not knowing this information at all (being that if I was oblivious to what works than I would not be so wrapped up in trying to follow it?)

I could probably loose about 20 pounds or so, I do look the same as my pictures but I do understand what you mean by how it impacts flirting. Although it is all confidence it does help when you know that you are at your best physically. Do you have any advice on gauging her intrest in getting physical after a drink or two, It does seem like certain women make it easy but the trouble I have is pushing it to flirting when it seems that they are not about it (maybe this is just in my mind and how it see her)

What was your experience on the second or third date ? How many have you been on? Do you try to get touchy early and how do you gauge whether it is to soon?