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Summary
Again and again, Castiel must watch Dean die as the Empty dangles happiness before him, only to rip it away. There is no escape; this is the reality he accepted to save Dean. His fate, his destiny, is to watch Dean suffer while he is forbidden from changing his fate—to stand there as his happiness destroys them.
Dean, meanwhile, makes a drastic choice. He wants his apple-pie life; he wants to be happy… but he wants it with Castiel. He’s sent to the empty, facing down a Castiel who doesn’t remember their real life, while the Empty kills him again and again right before Castiel’s eyes.
All of this, with the simple goal of staying alive long enough for Jack to get them out.