He goes to the same school as me, but I am not ready to strike a conversation with him out of the blue. I am afraid he will judge me, etc.

But he seems to always want to start a conversation but is shy to initiate one.

Should I wait for him to approach me? Or should I say something? and if so, what?

I am afraid that once he gets to know me, he won't like me & he will never realize how much I like him!

We have seen each other around at school many times and he always stares at me!