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Summary
Zachariah sent Dean to the future to show him how the apocalypse would go for humanity if Dean refused say yes to Michael. And Dean saw. Other him made damn sure Dean knew exactly how bad things got for Cas. When they went to kill the devil, Cas made it out alive and Dean somehow managed to drag him into the past with him. But what was he supposed to do with a broken ex-angel he didn't know how to help? Or a suddenly jealous Castiel?
Honestly, Dean didn't have a goddamn clue, but sink or swim, he needed to figure it out.
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“I’m beggin’ you. Say yes.” He said desperately, impassioned, before he shook his head, resigned, at his younger self. “But you won’t. Because I didn’t. Because that’s just not us, is it?”
Guiltily, Dean looked away, jaw clenched, because in spite of all he’d seen. All he’d been told, he still couldn’t imagine himself saying yes. Killing half the damn planet. Even now that he knew what would happen if he failed, he just couldn’t accept it as the only option. He'd find another way, he had to.