"What the hell?" Dean demands.
"I don't know," Sam says.
His brain is in overdrive trying to piece this together. What is the Trickster playing at? They agreed to leave Dean out of this. Sticking them both in a TV show sure as hell isn't leaving him out of it in the slightest -- and, given that Sam just caught him watching it this morning, it almost seems like this is for Dean. None of this makes sense.
"No, seriously, what the hell?" Dean asks again.
"I don't know!" Sam repeats.
"One theory," Dean prompts. "Any theory."
"Uh..." Sam sighs and just spits out the first thing he can think of. "The Trickster trapped us in TV Land."
"That's your theory? That's stupid."
"You're the one who said we're on Doctor Sexy, M.D.," Sam reminds him
"Yeah, but TV Land isn't TV Land," Dean says. "I mean, there's actors and lights and crew members, you know? This looks real!"
"It can't be," Sam says quietly. He knows the Trickster can whip up some very real things, but not like this. Not a whole world based on a TV show. He stops his brother once they've turned the corner, carefully staying out of everyone's way while they go ahead through their horribly-scripted soap opera day. "Dean, how can this possibly be real?"
"I don't know, all right?" Dean just happens to look away as a woman walks by -- possibly one of the ones they saw earlier; she looks vaguely familiar. "Oh, but there goes Dr. Wang, the sexy but arrogant heart surgeon."
Sam just stares at him uncomprehendingly.
"Oh, and there's Johnny Drake," he adds, looking down the end of the hallway at the man sitting on a hospital bed in the middle of the hallway, because why wouldn't there be a man sitting on a hospital bed in the middle of the hallway? "Oh, he's not even alive. He's a ghost in the mind of --" He cuts himself off as another doctor walks by to talk to -- and possibly flirt with -- the guy. "Of her, the sexy but neurotic doctor over there."
"So, this show has ghosts?" Sam scoffs. "Why?"
"I don't know," Dean admits. "It is compelling."
"I thought you said you weren't a fan," Sam reminds him. This definitely explains why he's suddenly become an encyclopedia of useless information.
"I'm not," Dean says immediately.
Sam just looks at him expectantly.
"I'm not!" Dean repeats.
He looks away, probably to ignore Sam's judgemental look, but something clearly catches his eye because his jaw drops. He looks like a child walking into his first candy store, which, under any other circumstance, Sam would probably laugh at, but right now, he's just confused.
"Oh, boy," Dean says quietly.
"What?" Sam asks.
"It's him," he whispers.
"Who?"
Dean turns back to look at his brother, giving off some very strong deer-in-the-headlights vibes. "It's him. It's Dr. Sexy." He swallows hard and looks at the floor, flustered.
Sam looks over to see a man walking towards them, who, Sam reasons, must be Dr. Sexy. He would have assumed Dr. Sexy would be a girl based on Dean's reaction, but Dean looks like he wants to go cliff diving right now, and it definitely seems like the Trickster's brand of humor to bring his soap opera idol to meet him.

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Reading Between The Lines (Sabriel)
FanfictionSabriel is the weirdest crack ship Supernatural canon has ever seen. And yes, it's canon. The Trickster brings Dean back from the dead, but for a price. He isn't asking for much. Unlike a demon, he's got no use for souls. He just wants some company...