Lauren,

I don’t see anything that you have shared here on what you get out this “friendship.”  Your words are all about being annoyed or worse by him.  You seem to be intimately involved in his personal life which sounds like co-dependence.

I know what I get from each friend that I have (single, married, coupled) and I don’t track or involved in any of their lives to that minute degree like you seem to do with him.

Don’t you have other people to have fun with? to talk with?  It seems like you have too much attachment to him to be at peace and actually enjoy a friendship with.

Mark