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I'd just about kill for the canonical backstory on this statement. 2014 Cas was so different, so damaged - so differently damaged to his timeline-equivalent Dean, who's all hard edges and cold purpose. Yet the episode implies they've made the journey together.

What left Endverse!Cas soft and bleak and open and emotionally articulate? Did he crawl through broken glass hell to get here, dragging himself up from nowhere to achieve this level of function and resignation, or has it been a slow, blurry slide from grace into decadence with the bumps softened to meaningless by drugs, booze, and orgies? Why does he package the last one with the 'love guru crap' as if there's still a point to existence, a meaning beyond the moment, then act with Dean (both Deans) as if there isn't? And when did 2014!Dean stop looking at him the way 2009!Dean does?

THE END (5x04)