- Randall: How did you wind up in here?
- Sam Winchester: I've got a brother who's an idiot.
- Randall: That'll do it.
- Dean Winchester: [takes his meal tray and sits opposite a very large and scary looking inmate in order to start a fight] Save room for dessert, Tiny.
- [chuckles]
- Dean Winchester: Hey, I wanted to ask you, 'cause I couldn't help but notice you are two tons of fun... just curious, is that just a thyroid problem? Or is that just some deep-seated self esteem issue? 'Cause y'know, they're, uh, just doughnuts. They're not love.
- Sam Winchester: You heard in the yard?
- Dean Winchester: Yeah.
- Sam Winchester: Dean, doesn't it bother you how well you seem to fit in here?
- Dean Winchester: No, not really.
- Sam Winchester: [as they walk into the prison] This is, without a doubt, the dumbest, craziest thing we've ever done... And that's in a long, storied career of dumb and crazy.
- Dean Winchester: Calm down. It's all part of the plan.
- Dean Winchester: Well my roommate doesn't say, how's yours?
- Sam Winchester: He just keeps staring at me in a way that makes me really uneasy.
- Dean Winchester: Sounds like you're making new friends.
- Dean Winchester: You sure about this?
- Sam Winchester: Pretty sure.
- Dean Winchester: Yeah, well, considering the circumstances, I'd like to do better than pretty sure.
- Sam Winchester: Okay. I'm really pretty sure.