I've been in this rut before with women relationship wise. Why are you so sadistic nibbling at "bits of his inner struggles" as you say, that's creepy as hell why are you being so emo. Everything you just said he most likely thinks about you and is trying to express sympathy for your disposition in relation to himself. If you were in anyway a good friend you would kick him while he is down and laugh about it. Or better yet just random acts of indirect violence. Show him you care with anger. Tell him you aren't taking this rubbish and will shit on his dead mama's grave if he keeps it up! He could use the Adrenaline and perhaps a few other hormones try sardines, chocolate, apples good pick me ups. Pull a few one liners from Tyler Perry's Madea. I would recommend some orchestra and symphonic metal music to get things going.