I usually like to show a lot of leg, of course my 7" jump boots add that little zing that makes men turn their heads. Once they're looking I simply start the conversation, Hi sailor looking for love? Now, how bout you?
First find out if he's already got a girl, then be he's friend. Find out what he likes you know kinda figure it out by conversation starters like "so what's your fav color or food" after those and some more have been answered you can move on to more personal questions like what do you look for in a girl. But don't go to fast, don't go to slow either. Then more and more you'll get to know each other and you'll began to trust each other and he will most likely like like you so you gotta ask him out and if your not looking for a boyfriend then just sick with that really good friend bond :)