Pardon to say this but you are friends with the most immature 24 year old moron out there known to humanity. Yes, if you didn't guess already but that was my judgement on him based on the facts you provided.

If he is sincerely your 'friend' then by all means, he ought to know where to draw the line. Unfortunately, bless his poor conscience, he's unable to think straight and is inevitably instigating the closest person (you) that will make him lose a friend without realizing what he did wrong.