I am scared to flirt with girls.

I don't have any issue talking to girls when the intent is not romantic/sexual. OK I have met someone, first few conversations went alright, how do I transition to something else without being embarrassed and feeling like a dick? Like, if I want to say something technical or communicate for something else, everything is fine. Otherwise, I feel very embarrassed and feel like I will be disgusting to her if I said something... I guess it is me trying to be OK with everyone and not have more people hate me... I don't know if I can take any more people hating me... makes me feel worthless...