YES YES, oh god, and that would be a big part of why Cas really doesn't like him. Partly Cas doesn't like this enabling of torture. Partly he's feeling rather >:-/ at Dean and Daryl becoming better friends. And when Cas confronts Dean about it, Dean throws 4x16 back in his face. You made me, Dean says. You made me because you didn't want to do it yourself, and now it's the same fucking shit all over again, well fuck you.

Blathazar is totally curious as to who the the man who changed his once-uptight friend is.
Toooootally. He'd be like, "How did you do it, Dean? Tell me your secret."
"I don't have any secrets."
"I don't believe that for a moment."

When it says that Sam is gonna take Bobby's blood... does that mean Sam is gonna have to kill him?! D: