How do you start a conversation with a shy guy?

I am one of the most outgoing people I know, and my boyfriend of over a year now is incredibly SHY! I liked him for almost two years before he even decided to ask me on a date, which got me really frustrated. Sometimes, guys like that just seriously have no clue how to handle girls and are probably even afraid of rejection. Don't be afraid to make your feelings VERY OBVIOUS....he might need you to be that way =]