Castiel: It's very complex. If the pizza man truly loves this babysitter, why does he keep slapping her rear? Perhaps she has done something wrong.
Dean: Are you watching porn? Why?
Castiel: It was there.
Dean: You don't watch porn in a room full of dudes. And you don't talk about it. Just turn it off. Well now he's got a boner.

[to a demon] You gonna kiss me?

Dean

Guess I kinda lost my head.

Crowley

Dean: Until we get you back on your soul train, I'll be your conscience.
Sam: So you're saying you'll be my Jiminy Cricket.
Dean: Shut up. But yeah you fricken puppet, that's exactly what I'm saying.

Dean, did you service Oberon, King of the Fairies?

Sam

Nipples?

Dean
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Sam: So you're saying having a soul equals suffering?
Dean: Yes, that's exactly what I'm saying.

Sam: What about when there are no more leads for that? I mean are you just supposed to sit there in the dark and suffer, even when there's nothing that can be done at that moment?
Dean: Yes! You sit in the dark and you feel the loss.
Sam: Absolutely, but couldn't I just do all that and have sex with the hippie chick?
Dean: No!

Dean: They're after me!
Sam: Third kind, already? You better run, man. I think the fourth kind is the butt thing.
Dean: Empathy, Sam. Empathy!

You want to be a real boy Pinocchio; you've got to act the part.

Dean

Fake it 'til you make it.

Dean

Dean: You don't care. You have to care.
Sam: About what exactly?
Dean: About everything!

Supernatural Quotes

Why do they call this place The Empty? It's full. It's full of sorrow and despair playing over and over again of angels and demons dreaming about their regrets. Forever.

Ruby

Weird, creepy, off-the-grid "Children of the Corn" people? Yeah, I’m in.

Dean