The Mayor ,'End of Days'
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3x6
Bela: You know, when this is over, we should really have some angry sex.
Dean: Don't objectify me.
...
Sam: How do you sleep at night?
Bela: In silk sheets, rolling naked in money.
...
Dean: A Hand of Glory? I think I got one of those at the end of my Thai massage last week.
Also DaLDoM, S3, but it's dialog rather than mono--
Dean: Dude, you were making some serious happy noises. Who were you dreaming about?
Sam: What? Nothing. Nobody.
Dean: Come on, you can tell me. Angelina Jolie?
Sam: No.
Dean: Brad Pitt?
Sam: No!
3x5
Dean: I'm going to stop the big bad wolf, which is the weirdest thing I've ever said.
4x03 Dean: On November second 1983, don't get out of bed. No matter what you hear, or what you see. Promise me you won't get out of bed.
4x03 Dean: Hey, I wanted to tell you, you know for what it's worth. Um...it doesn't matter what your Dad thinks, I like that John kid.
3x3
Dean: What the hell is wrong with you!? You don't just go around shooting people like that!
Bela: Relax, it's a shoulder hit, I *can* aim.
3x4 Casey: Do you believe in god, Dean? I'd be surprised if you did. Dean: I don't know. I'd like to.
2x18
Dean: What's a P.A.?
Sam: I think it's kinda like a slave.
The Kids are All Right, S3
Neighbor: 'The' Dean? Best weekend of my life Dean?
Dean: Heh, Gumby Girl. Does that make me Pokey?
2x16
Dean: You know, just once I'd like to round the corner and see a nice house.
2x14
Dean: Dude you... You like full on had a girl inside you for like a whole week.