Castiel: When Jack was dying, I... I made a deal to save him.
Dean Winchester: You what?
Castiel: The... The price was my life. When I experienced a moment of true happiness, the Empty would be summoned and it would take me forever.
Dean Winchester: Why are you telling me this now?
Castiel: I always wondered, ever since I took that burden, that curse, I wondered what it could be, what... What my true happiness could even look like. I never found an answer. Because the one thing I want... it's something I know I can't have. But I think I know... I think I know now. Happiness isn't in the having. It's in just being. It's in just saying it.
Dean Winchester: Well, whatever Chuck did to Amara, he's probably more powerful than ever. Billie wants us dead, Jack's powerless, and Michael's not returning our prayers. So we have no heavy hitters on our side. We're basically at zero.
Sam Winchester: We'll regroup somehow.
Dean Winchester: Right. Yeah, to somehow.
Chuck: You know, I tried and I tried and I tried, but you're all just too stupid, too stubborn. Too broken. You know what? I'm over it. I'm over you.
Sam Winchester: Yeah? Good.
Dean Winchester: Screw you, Chuck.
Chuck: No, screw you. You know what you do with broken toys? You throw them out. So, kill each other, don't kill each other... I don't care.
(Dean aims his gun at Sam...)
Dean Winchester: Chuck has to die. He has to! Otherwise he'll keep us tap dancing forever, and I can't live like that, man! I can't live like that! I won't!
Sam Winchester: I know you feel like that right now, okay. I know you do. But you gotta trust me. My entire life, you've protected me... From Dad, from Lucifer, from everything. I didn't always like it, you know, but... it's the one thing in the whole world that I could always count on. It's the only thing I've ever known that was true. So please... put the gun away. Just put it away, and we'll figure it out, Dean, we'll find another way, you and me. We always do.
(Dean puts away his gun...)
Chuck: Are you kidding me?! After everything, all that, you... you did it again!
Dean Winchester: What I said to Sam, you didn't need to hear that. Alright? Not now. Not with the weight that you're carrying... For us, for this world. Jack... I don't know how to explain it, but what I found out about Chuck... it's like... It's like I wasn't alive. Not really. You know, like, my whole life I've never been free. But like, really free. But now... now me and Sam, we got a shot at living a life. Without all this crap on our backs. And that's... That's because of you. So, I... I... I wanted to say... I need to say... Thank you, Jack. Thank you.
Jack: You're welcome.
Sam Winchester: Does any of this feel right to you?!
Dean Winchester: It doesn't matter how we feel! You know what? Stay. Stay. But somebody's gotta be the grownup here.
Sam Winchester: Yeah, well, someone has to keep fighting for Jack.
Dean Winchester: He knows what he signed up for!
Sam Winchester: Last I checked, we don't give up on family.
Dean Winchester: Jack's not family! I know how you feel about the kid, okay. I care for him, too. I do. But he's not like you. He's not like Cas. He's just not.
Jack: I'm... I'm ready.
Dean Winchester: So that's how it's gonna be? You give me the silent treatment?
Sam Winchester: I'm not sure what you want me to say.
Dean Winchester: That you get it. Like, I said, killing Amara, Jack dying... That's the only way.
Sam Winchester: "The only way. Our one shot, our last chance." You ever get tired of saying stuff like that?
Dean Winchester: We don't have to like it, alright, but you and me, we gotta get it done.
(Castiel is thinking about going to investigate a potential case with Jack...)
Dean Winchester: Just get out there, you know, stay busy.
Castiel: With a murder investigation?
Dean Winchester: Yeah.
Sam Winchester: Dean's not wrong. And, look, this case, uh, maybe you can help.
Dean Winchester: Alright, well, you guys go "Highway to Heaven" that bitch.
Jack: I'll get my suit. Can we wear matching ties?
Castiel: Yeah. Blue's a good color on you.
Sam Winchester: There's gotta be something, some way. Whatever it is, I'll do it. Don't, Dean. I'm not gonna let you go to hell.
Dean Winchester: Yes, you are! Yes, you are. I'm sorry. I mean, this was all my fault. I know that. But what you're doing is not gonna save me. It's only gonna kill you.
Sam Winchester: Then what am I supposed to do?
Dean Winchester: Keep fighting. Take care of my wheels. Sam, remember what Dad taught you. Okay? And remember what I taught you.
Sam Winchester: You know, if this doesn't, uh... If this doesn't go the way we want...
Dean Winchester: No, no, no, no, no, no.
Sam Winchester: "No" what?
Dean Winchester: You're not gonna bust out the misty goodbye speech, okay? And if this is my last day on earth, I do not want it to be socially awkward. You know what I do want?
(Dean turns on the music)
Sam Winchester: Bon Jovi?
Dean Winchester: Bon Jovi rocks... on occasion.
(Sam and Dean sing "Wanted dead or alive" by Bon Jovi)
Dean Winchester: Sam, we are not gonna make the same mistake all over again.
Sam Winchester: You said that, but what does that mean?
Dean Winchester: Don't you see a pattern here? Dad's deal, my deal, now this. Every time one of us is up the creek, the other's begging to sell their soul. That's all this is, man. Ruby's just jerking your chain down the road. You know what it's paved with, and you know where it's going.
Sam Winchester: Dean. What are you afraid is gonna happen? This is me, I can handle it. And if it'll save you...
Dean Winchester: Why even risk it?
Sam Winchester: Because you're my brother. Because you did the same thing for me.
Dean Winchester: I know. And look how that turned out. All I'm saying... Sammy, all I'm saying is that you're my weak spot. You are. And I'm yours.
Sam Winchester: No, you don't mean that. We're family.
Dean Winchester: I know. And those evil sons of b*tches know it too. I mean, what we'll do for each other, you know, how far we'll go. They're using it against us.
Sam Winchester: So we just stop looking out for each other?
Dean Winchester: No, we stop being martyrs. Man, we stop spreading it for these demons. We take this knife and we go after Lilith our way. The way Dad taught us to. And if we go down, then, uh... then we go down swinging. What do you think?
Sam Winchester: I think you totally should have been jamming "Eye of the Tiger" right there.
Dean Winchester: Oh, bite me. You know, I totally rehearsed that speech too.