What do you do when the guy you like always asks people out as dares?

well, you should really ask the guy out because you like him and want to be with him and not because of a dare. And don't chicken out, you have the chance to ask him out, take it because later on he might have another girlfriend. Don't be afraid and i know its hard, but just keep reminding yourself that he might like you back. What will happen if people won't take chances? We would probably just lying down with nothing. I'm not trying to bring you down, but just try it. Life is what you make it ;).