Hard to be altogether too worried about it when it can't come back to bite him. He's dead. Whatever happens from this point on is some other hunter's problem, whether Dean likes it or not. He's embracing the ultimate retirement.

—except any single person who knows him could tell him how full of shit he was. Not a word of that's true. If anybody were inclined to claw their way back from beyond the grave to continue doing work he hates, it's Dean Winchester. And there's plenty of opportunity for it to come bite him here, in his replacement afterlife. He's trying not to think about any of that too hard.

After a heavy weight of silence, he finally pushes off the edge of the bar. One slow, deliberate step erases the distance between them again, so he can settle a careful hand on Michael's shoulder.

"I'm sorry your dad disappointed you. I'm sorry he was an asshole, and I'm sorry you had to lose him the way you did. Nobody should have to live through that. Not even you. You deserved better."

For all their differences, for all the things he dislikes about Michael, for all the times they were on opposite ends of an issue... all of that, at least, he can say honestly.

He has nothing else to add on the subject of Chuck — it's better that the guy become a footnote. He thinks it's more fitting to make that douchebag as irrelevant as possible.