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Sam: Oh, and you might also want to mention that other thing.
Dean: What other thing?
Sam: The serious unfinished business. Dean, what is going on between you two?
Dean: Alright, so maybe we were a little bit more involved than I said.
Sam: Oh, OK. Yeah.
Dean: Okay, a lot more. Maybe. And I told her the secret about what we do, and I shouldn’t have.
Sam: No, look, man, everybody’s gotta open up to someone, sometime.
Dean: Yeah, I don’t. It was stupid to get that close, and look how it ended. Would you stop? Blink or something.
Sam: You loved her.
Dean: Oh, God.
Sam: You were in love with her, but you dumped her. Oh, wow. She dumped you.
Dean: Get in the car.
Route 666 [1.13]
Dean:Cas, you got your ears on? Listen, you know I am not one for praying, ‘cause in my book it’s… it’s the same as begging. But this is about Sam, so I need you to hear me. We are going into this deal blind… and I don’t now what’s ahead. Or what it’s gonna bring for Sam. Now, he’s covering pretty good, but I know that he is hurting, and this one was supposed to be on me.So, for all that we’ve been through, I’m asking you… you keep a lookout for my little brother, okay?
[8.16] - Remember the Titans
Tortured Sam: I wish you hadn’t come, Sam.
Sam: I had to. I’m here, right? Out there in the real world, I’m at Bobby’s, aren’t I?
Tortured Sam: How do you know?
Sam: This whole time, I’ve smelled nothing but Old Spice and whiskey. Figured if I could get back here, back to my body I could, I don’t know, I could snap out of it somehow.
Tortured Sam: First you have to go through me.
Tortured Sam: Humpty-dumpty has to put himself back together again before you wake up. And I’m the last piece.
Sam: Which means I have to know what you know. What happened in the cage?
Tortured Sam: Trust me. You don’t want to know it.
Sam: You’re right. But I still have to
Tortured Sam: Sam, you can’t imagine… Stay here. Go back, find that bartender, go find Jess, but don’t do this. I know you. You’re not strong enough.
Sam: We’ll just have to see
Tortured Sam: Why is this so important to you?
Sam: You know me. You know why. I’m not leaving my brother alone out there.
Tortured Sam: (picks up a knife and holds it out to Sam) I’m not gonna fight you. But this is your last chance. (Sam takes the knife.) Good luck. You’re gonna need it. (Sam stabs him, absorbing his memories.)
[6.22] - The Man Who Knew Too Much
Dean: We’ve been down roads like this before, man. With Yellow Eyes, Lucifer, Dick Friggin Roman … we both know where this ends: one of us dies. Or worse.
Sam: So you just up and decided it’s going to be you
Dean: I’m a grunt, Sam. You’re not. You’ve always been the brains of this operation. And you told me yourself, you see a way out. You see a light at the end of this ugly ass tunnel. I don’t. But I tell you what I do know, is that I’m going to die with a gun in my hand. Because that’s what I have waiting for me, that’s all I have waiting for me. I want you to get out. I want you to have a life, become a Man of Letters, whatever. You with a wife, kids, and grandkids, living out until you’re fat and bald and chugging Viagra. That is my perfect ending and it’s the only one I’m gonna get. So I’m gonna do these trials and I’m gonna do them alone. End of story. You stay here. Call if you need me, but if you try to come after me I will shoot you in the leg.
-Trial and Error [8.08]
Castiel: [while trying to play “bad cop” screams into a woman’s face] Why did you kill your husband?!
[later - Dean has pulled Castiel aside]
Castiel: What? I was being ‘bad cop’
Dean: You were being ‘bad everything’
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