I'm not a dating expert. Neither do I have impeccable game. I used to over analyze every situation and watch what I said, afraid of saying something stupid. In addition to being a slight introvert, this made approaching others hard.

I've recently adopted the attitude of "I don't care whether she likes more or not, I'll still be the same." I've stopped planning my words and just approach others. If I get a negative response, I stay positive and move on. I'm still the same 5'10 guy but having this mindset has helped me loads.