Well if the guy is shy you should confront him as a person he'd like to get to know. But you let him ask you out. Just wait for a while and try to seem like you two are compatible and then when the time is right, start hinting him that you like him and wait for the reaction. This way both of you will get 1-ups on your confidences =). In the ideal event, he will ask you out, you two will have a perfect relationship, and no more shyness. But most likely you two are two shy to say anything, in which case you should keep hinting that you like him and make the first move. It's still ok for you to ask him out and not the other way around. It happens to a lot of people and to justify my reasoning I simply have to say this; "A relationship is a cooperation between two people, not one. If one person isn't cooperating, it's no longer a relationship, but a simple case of selfishness." What I mean, in less Confucius crud, you're going to have a rough relationship if you expect him to do everything first. Remember: Guy+Girl=Relationship, Relationship-you=himself, Relationship-him=yourself.=)