How can I flirt with a guy I know and like on msn messenger without sounding stupid or childish?

Question

I really like this guy and I guess this might be easier because he knows...well...he thinks he knows. What type of questions should I ask him? For example "Where did you get that fantastic smile?"

Answer 1

when you flirt it always sounds lame, anything you say sounds lame, but as long as you say it with confidence is what matters. if you sound childish and giddy while saying whatever you are thinking of saying then you will feel... well lame, but if you say it with confidence then you won't feel, nor sound stupid.