Girls and Guys, I have a guy problem!!!?

Ok, so I like this guy and we are pretty comfortable around each other. Like we can make jokes and stuff and laugh about things together so I would say we are friends, but like new friends. He also is comfortable telling me about himself and like what he does for fun, etc. I don't know him that well other than what we have talked about, but I want to ask him to hang out. How should I do this, guys how would you like a girl to ask you out? Also I want to look subtly a little bit nicer than usual. Girls, how can I do my makeup to make it look casual, but get him to notice that I'm pretty.