Dean: And by the way, how you doing?
Bobby Singer: Doing?
Dean: Yeah. You know, just... in general.
Bobby Singer: Oh, you mean my legs. I'm just weeping in my Haagen-Dazs. Idjit.

Dean: Bobby? What the hell are you doing here?
Bobby Singer: Planting daisies. What's it look like? Came in on the case.
Dean: And you beat me here?
Bobby Singer: Well, brains trumps legs, apparently.

Old Dean: Bobby's an idiot, that's what happened.
Bobby Singer: Hey, nobody asked you to play.
Old Dean: Right. I should have just let you die.
Bobby Singer: And for damn sure, nobody asked you to lose.
Sam: It's like Grumpy Old Men.
Bobby and Old Dean: Shut up, Sam!

Old Dean: You saw a chance to turn the hands of the clock back and get out of that damn chair. Pretty tempting. I can imagine.
Bobby Singer: No, you can't.
Old Dean: You got me. I never been paralyzed. But I tell you something--I've been to Hell, and there's an archangel there wanting me to drop the soap. Look at me! My junk's rustier than yours!

(to Sam)
Old Dean: Dude, I believe that he-witch gave you the clap.

Dean: You're family. I don't know if you've noticed, but me and Sam, we don't have much left. I can't do this without you. I can't. So don't you dare think about checking out. I don't want to hear that again.
Bobby Singer: Okay.
Dean: Okay. Good.
Bobby Singer: Thanks. Now, we done feeling our feelings? 'Cause I'd like to get out of this room before we both start growing lady parts.