Sam: Dad said they always had the perfect marriage.
Dean: It wasn't perfect until after (Mary) died.

Sam: Heaven?
Dean: Yeah.
Sam: Okay, how are we in Heaven?
Dean: All that clean living, I guess.

Go ahead, Roy. Do it. But I'm gonna warn you--when I come back, I'm gonna be pissed.

Dean

What are you, the Hamburglar?

Dean

Why does Heaven care if Harry meets Sally?

Dean

Unleash the Kraken. See you tomorrow morning.

Sam

Dean: Hey, when I want to drink, I drink. When I want sex, I go get it. Same goes for a sandwich or a fight.
Castiel: So... you're saying you're just well-adjusted?
Dean: God, no. I'm just well-fed.

Sam: Dean, enough!
Dean: What?
Sam: You just punched a Cupid!
Dean: I punched a dick!

Cupid: Love is more than a word to me, you know? I love love, I love it! And if that's wrong, I don't want to be right!
Castiel: Yes, yes. of course. I, uh... I have no idea what you're saying.

Dean: Cherub?
Castiel: Yeah, they're all over the world. There are dozens of them.
Dean: You mean the little flying fat kids in diapers?
Castiel: They're not incontinent.

Dean: Where am I going?
Sam: Dean, it's Valentine Day. Your favorite holiday, remember? I mean, what do you always call it - uh, Unattached Drifter Christmas?

Castiel: This is their handshake.
Dean: I don't like it.
Castiel: No one likes it.

Supernatural Season 5 Quotes

Endings are hard. Any chapped-ass monkey with a keyboard can poop out a beginning, but endings are impossible. You try to tie up every loose end, but you never can. The fans are always gonna bitch. There's always gonna be holes. And since it's the ending, it's all supposed to add up to something. I'm telling you, they're a raging pain in the ass.

Chuck

Dean: Where's Cass?
Chuck: He's dead. Or gone. The archangel smote the crap out of him. I'm sorry.
Dean: You're sure? I mean, maybe he just vanished into the light or something.
Chuck: Oh, no. He exploded. Like a water balloon of chunky soup.