What makes a good flirt? Confidence, humor, and playfulness. Then you just roll with it... and if all those things are going good, you'll be flirting like a pro and it will be obvious but humorous and not too serious so she doesn't feel awkward or out of place. I'm not that great at it but my friend is a pro. I do alright if I'm in a really good mood and feeling playful as long as I'm not thinking about it too seriously. Ya think about it, forget it, pack up and go home cause it's done. It'll be obvious but not in a good way and you'll sound like a bumbling fool.