What does he mean by this?

If it's really hard for you to talk to him in person you should try writing him a note. Also, try hanging out with his friends as well as your friends. It's easier to open up to someone with there are people around because it makes everything less awkward and you won't feel as shy. Eventually one of you is going to have to make the first you, and if you REALLY like him than you'll take the chance!:)