I think the ending of Don/Dick’s tale in Mad Men should have some reconciliation of these two identities without betraying the character we’ve been watching for six seasons. You’re completely right that any romantic ending where he is off the booze & in a happy relationship with a woman and his children would be a betrayal. I’m fine with Don not being an alcoholic, but I think romantic fulfillment in any lasting sense is simply an impossibility for the character. The same with real friendship. I’d like to see him have his moments of happiness and connection with others, but the series simply has to end with the understanding that it is fleeting.

Finally, season six left us with a Don Draper realizing he was creatively unfulfilled by his career in advertising, as well as his personal creation of Don Draper. This is a character who has always been driven by creativity, and in his best moments used that creativity to address the pain of his childhood and question of who he is. Will we see him try to do this in a different form than an advertisement? How will he find creative fulfillment away from the agency and drink? My instinct is to say that I’d love to see him find resolution and clarity by writing a great book, then return to his boozing and womanizing ways as he’s swept away by its success. It would be a sad way to end the show, but it would remain true to the character and his world.