Personally , I would find it a compliment and I think flat out telling him you want to get to be closer is the first thing you should say. This will tell you if he is interested in you. If he makes up excuses, move on. This way you don't get hurt so bad. I hate to say it but men are visual, so looking your best and sexiest is also a good idea for asking this guy if he is interested in you. I don't think there really i s a fun way, it is stressful to you, so just blurting it out and laughing could make it less tense. Good Luck..