[revenge is supernatural] I'm busy in the blissful unaware
Dean knows when he's been whammied, a lot of the time Most of the time, actually.
Well, seventy-five percent of the time.
He used to be able to tell when he's being whammied. Then he started to work for Fringe Divison, and that percentage went down quite a bit. There were ways of being whammied that he hadn't even thought of and he was doing his best to distinguish between the two. He had thought he was doing pretty well with all of it. At least, until he walked into his hotel room after having drinks with Anna and found Azazel standing there.
Then he promptly proceeded to flip the fuck out.
First of all, he wasn't sure how he got in there. He might have been seventy-five percent out of the game, but he still salted all his doors and windows, so this was very much a no demon zone. Follow that up with the fact that he shot Azazel, right in the heart, three years ago, Dean was starting to wonder if his and Sam stopping the Apocalpyse had gone a little screwy. If it did, Dean's life was about to start seriously sucking. Then there was a struggle, some confusion, and then Dean passed out like a whimpy girl for a reason he wasn't sure about. He knew what he saw. But Dean wasn't exactly trusting his eyes at the moment.
As Dean started to come to, he rolled into a sitting position and glanced around. He was still in his hotel room, but his head hurt like a bitch and ... well, there was a giant Sam doppleganger sitting in the other end of the room. Dean clearly hit his head harder than he thought, or Walter slipped him the happy drugs again. Either way, Dean was pretty sure he was fucked.
" ... This is ... new."