Sidewinder

I meet girls I sometimes wouldn't mine going out with, but I don't think it's right to ask a girl you just so happen to come accross on a date. I don't think I'll ever see these girls again so should I ask them out on a date? Or should I get to know them better by asking for a phone number or something? Whats the best way to handly these situations?

I get shy around girls. I never can't think of anything to say or talk about. What are some topics to start a conversation that girls like?