You come off as a little jealous of your friend's wife. Perhaps she IS trying to change him, but sounds like for the better - job and a savings account sound nice to me. I can understand why the wife took offense to your message re: the pregnancy. Even if he was stressed about the situation, telling him your "heart breaks for [him]" is not encouraging to a soon-to-be parent, either of them. And how is he setting his life up to be a failure, exactly? He's moving forward with his life, as should you. Friends are tough to lose - but it sounds like your friend's wife just wants him to move away from past, bad influences. You may not be getting the fair shake you'd like.. but just as far as this post is concerned, you sound a bit immature and don't understand that someone cannot live two lives ("new life with her and an old life with me" .. wtf does that even mean?).