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Dean is starting to feel hopeless. “We’ll lose” he says, “I just led us into another trap, all because I couldn’t hurt Chuck. Because I was angry and because I just needed something to kill, and because that’s all I know how to do.” That’s what he’s always been, it's what John raised him to be, a killing machine. Just kill the monster. Chuck is the monster.
Castiel interrupts his thoughts. “Dean”
“It was Chuck all along. We shouldn't have left Sam and Jack. We should be there with them right now.” His voice softens as he begins to tear up. “Everybody's gonna die, Cas. Everybody. I can stop it. She's gonna get through that door.
Dean and Castiel move towards each other. As if to find comfort in each other in their last moments.
“I know,” Castiel says.
“And she's gonna kill you and then she's gonna kill me. I'm sorry.” Dean is hopeless. There’s nothing he can do.
Castiel suddenly has a realization. “Wait there is, there is one thing she's afraid of. There's one thing strong enough to stop her.”
Dean is confused. What could Billie be afraid of? She’s literally Death.
Castiel continues, “when Jack was dying, I made a deal to save him.”
“You what?” Why didn’t he tell him? That is important to know.
“The price was my life. When I experienced a moment of true happiness, The Empty would be summoned and it would take me… forever.”
“Why are you telling me this now?” Is he going to summon it now? ‘True happiness’ Is he happy here? This doesn't make sense.
Castiel is starting to tear up. How is he happy?
“I always wondered, ever since I took that burden, that curse, I wondered what it could be? 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. “
Saying what? What can’t he have? What is he talking about?
“What are you talking about, man?”
“I know. I know how you see yourself, Dean. You see yourself the same way our enemies see you. You’re destructive, and you're angry, and you're broken. Your ‘daddy's blunt instrument’. And you think that hate and anger, that, that's what drives you, that's who you are. It's not. And everyone who knows you sees it. Everything you have ever done, the good and the bad, you have done for love. You raised your little brother for love. You fought for this whole world for love. That is who you are. You are the most caring man on Earth. You are the most selfless, loving human being I will ever know.”
Dean’s mind is racing. Why is he saying all this? Why hasn't he ever said this before? Is he saying goodbye? He’s crying but he was just talking about his happiness.
“You know, ever since we met, ever since I pulled you out of Hell… Knowing you has changed me. Because you cared, I cared. I cared about you. I cared about Sam, I cared about Jack… I cared about the whole world because of you. You changed me Dean.
Cas is shedding tears. Dean says quietly, almost in a whisper, “Why does this sound like a goodbye?” He can't bear to lose Castiel. It hurts more and more every time.
“Because it is. I love you.”
That’s his true happiness? He loves me? He’s smiling now. He’s smiling and he's crying. He's happy. He’s going to leave.
Castiel puts his bloody hand on Dean’s shoulder. Just like he did over a decade ago.
“Goodbye Dean.”
He throws Dean across the room away from the danger, away from The Empty. His final living act is to save Dean’s life. Dean watches Castiel as he smiles while being sucked into the void along with Billie. Dean is left alone with his thoughts and the fresh memory. He’s left with this love confession that he could never respond to. There was no time. There was too much to say.
Bille is gone, she cant hurt him anymore, but why does his heart still hurt? He cries while sitting on the dungeon floor. He ignores Sam’s phone calls. He can't talk to anyone else right now. He doesn’t know how long he stays there.
In Despair.