Dean went to hell six months ago. Since then, it's just been you and Sam living in the bunker. He didn't know what else to do, so he quit hunting. He figured there was no point in hunting by himself, leaving you all by yourself in the bunker or dragging you along with him and risking your safety.

He keeps you safe, he keeps you fed. He's been taking on different jobs, trying to provide for you. You can tell it's wearing him down; he works almost all day, coming home late at night and going to work early in the morning. He's still in a cycle.