Keep telling me the shittiest jokes you know. I promise that will help.

[Dean manages a small smile. This is really going to suck for both of them; he remembers only too well the conversation he had with Wynonna after her stint of being tortured by Lucifer, and it seems like an especially cruel twist to have her on the other side of that equation now.]

And when this is over, promise me we'll get drunk and shittalk every asshole demon and Lucifer.

[He watches as she picks up the list of his sins. There's...a lot on there, and, actually, he's still surprised the list is as short as it is; he feels like maybe it skipped a few. Regardless, all of those sins that are on there? Dean knows deserve to be there.]