Hearing Leonard’s story of feeling overlooked and unloved causes Don to break down crying, recognizing himself in those words. But then there’s the conversation with Leonard, which is in many ways the turning point of this episode, and a major milestone in the life of Don Draper/Dick Whitman. That he hadn’t really changed all that much. That Don instead simply went back to being Don, and doing the one thing he was always good at. So as Mad Men ends, with a smiling Don seemingly finding spiritual side, did he achieve true inner peace? That’s where the Mad Men finale comes in, with Don’s retreat centered around him finding not just a sense of purpose, but an idea of who he really is and being happy with that. Elsewhere, Mad Men’s ending attempts to give relatively happy conclusions for most of the other characters: Peggy decides to stay at McCann Erickson, Joan starts her own production company, Roger is happily married to Marie, Betty is dying, but she's doing it on her terms as much as possible, and Sally and the boys are going to be ok. In "Person To Person", the series finale of Mad Men, Don goes to a retreat in California, in an effort to find some kind of enlightenment after all the pain and suffering his lies have caused not only himself, but just about everyone he’s ever come into contact with. In the end, it does something a little quieter, more subtle, and very much in keeping with Mad Men as a whole. It’s never exactly clear what that is, which is why there were theories ranging from Don being DB Cooper to him falling (or jumping) out of his office window to his death. The final season of Mad Men is largely concerned with pushing Don Draper towards.something.
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