So we get stuck with Ms. Moneypenny.

Dean

Dean: Do I know you?
Becky: No, but I know you.

Rufus: We're here. Let's do this. Just like old times.
Bobby: Well, as long as I get to drive.
Rufus: Hell, no.

Rufus: I take it you know each other.
Dean: He's our grandfather.
Rufus: Somebody needs a hug.

We've been Parent Trapped.

Dean

[to Sam] My god, son. You're about as cold as they come.

Samuel

Dean: And how would you characterize their relationship?
Girl: Relationship? No, no, they weren't having a relationship.
Dean: Just the tone or the nature of their conversation.
Girl: Well... loud. And athletic?

Dean: So he came by here?
Girl: Oh, he came by a few times.
Dean: Did he? To uh speak to Nicole?
Girl: Right.

Whoa, this one's got a little bit of a wild side. It's all in the eyes, Sam. See it?

Dean

Is that Bobby Singer? Give him a kiss for me.

Crowley

Woman: I'm sitting like this so you'll look at my breasts. I just bought them. I need a lot of attention.
Dean: Good luck with that.

Bobby: Ok then, lets roll credits on this chick flick. You boys have a safe flight and uh, try some of the local grub. I hear it's exotic.
Dean: Oh yeah, no, definitely, we are. I hear they have an Olive Garden.

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