What can I do to break the ice?

Hmm...I guess I have this crush on this guy but I just can't seem to talk to him. I kinda ignore him but I really don't want to! I'm just extremely shy. Like this morning, I saw two of his friends that I normally talk to (They're my friends too I guess) and i went and sat with them and started talking about Spanish cl. But then he gets to school and heads straight for the table! I'm thinking in my head "OMG no way!" So he sits down with us, I totally freak out (in my mind haha) and tense up and I can't even say a measly hello. I can't talk to him but i can talk to his friends perfectly fine! Ugh. I just need to break the ice with him and somehow become one of his friends so I can try and flirt with him and see where things can go from there...Btw, because I'm shy with people I like, I can't really flirt either...Has this ever happened to you guys?? Please help me...what do I say? How can I start a conversation with him after saying hello? Do you understand where I'm coming from? Lol. If you have any stories that may help, I'm willing to read them. Please, I would be grateful for any kind of advice! :D Thank You!