PLEASE HELP! I need advise about my friend who i think is angry?

ok,here's the problem.my friend i think got mad at me and won't talk to me.i told him about this girl that liked him and how she isn't right for him and he said that he will delete me from his messenger list.if he meets her.and he was joking but i took it seriously.after that i asked him all sorts of rude questions and sorta said bad stuff to him and then i kept being annoying and saying what ever.and we were chatting at that point.then he just left me hanging and never responded any of my IMs.i sent him emails and IMs apologizing but he doesn't respond any of them.is he angry with me?what should i do?i don't want to lose this friendship with him.he is really nice and makes me laugh sometimes.usually i go on the computer to just chat with him.i don't want to lose a nice friend like him.PLEASE HELP!!