The season finale of Mad Men — satisfying, redemptive, devastating and in some ways, hopeful, as it was — still left a lot of questions about the lives of its characters unanswered. In many ways, Matthew Weiner seemed to be intentionally vague, leaving open several possibilities for the final season. The truth is that — besides an ultimate end point, which Weiner has already committed to — he doesn’t know how next season will go. He doesn’t know where the characters will be, or even in what year.
Indeed, Weiner is as clueless as the rest of us, as he tells Vulture in an interview: “I don’t know if we’re going to come back [in 1969]. I don’t know anything yet. I literally have to stop thinking about it, let the finale play out, and really get my head blank.” Weiner, as he has since the beginning of the show, takes the show one season at a time; each season is thematically self-contained. We don’t know where, or even when, his journey will take us, and because Weiner is notoriously secret about these things, we probably won’t even have the vaguest of ideas until next year’s season premiere.
That won’t stop us, however, from posing the questions, or from wondering where he might take us. Below is a series of open questions without any answers. No one knows those answers, but that won’t stop us from speculating.
1. Who is Lou Avery replacing? That’s a question that left some of us confused. When Don said, “You’re early” to Lou Avery and Duck Phillips, I had the sense that Lou was replacing Don. But the fact that Peggy was in Don’s office, and the pained expression on Don’s face when told that Ted would be overseeing Peggy from California suggests that Peggy is replacing Don. Does it even matter, because Don is expected back? Or is he? Will he reclaim his old position, or will he have to work his way up again to some degree? What does the office hierarchy look like when the show returns? Can Mad Men survive with Don outside of Sterling Cooper & Partners?
2. Is Sterling Cooper & Partners bi-coastal now? Pete and Ted are going to California. Harry’s there. Megan will likely be there. Stan wants to be there. That’s where the future lies, with television. Will there be a significant presence in California, or will Ted (and maybe Pete and Megan and Harry) become an occasional sideshow, like Betty? What about Detroit? Is there a third office in the making there, and will we see more of Bob? Weiner has said that there may be more to Bob Benson’s story.
3. Is Bob gay? That apron should be a dead give away, huh? Many of the signs, of course, point to yes: His short shorts, his relationship to Manolo, his pass at Pete. But was some — or all — of that part of a con? Part of Bob playing a character? Could he be romantically interested in Joan? Will there be a competition for Joan’s affections between Joan and Roger? And will Roger find a place within Joan’s life? Where is Manolo? Will he ever be prosecuted? Will Bob be implicated? We still don’t know exactly why Bob Benson decided to pull a Don Draper in the first place. What is in his past?
4. Will Trudy and Pete reunite? That’s at least what the season finale portends, that Pete had a moment of recognition, a moment where he flat-out realized that he completely screwed up his life. But can Pete change? Is he, like Don, doomed to repeat the same mistakes over and over until he’s forever alone? Will he keep poking at the Bob Benson hornet’s nest until Benson stings him to death?
5. Where is Sylvia? There have not been any repercussions to Sally’s discovery and Don and Sylvia’s affair. Is it really, finally over? Did her son, Mitchell, avoid Vietnam? Will anyone besides Sally ever catch Don in the act? Is she just another in a long list of Don’s mistresses that come and go without any longterm repercussions? Have Sylvia and Mitchell moved to Minnesota?
6. Are Megan and Don divorcing? At the end of the episode, Megan finally came to her senses and realized that there was nothing in the marriage worth fighting for, that she was not a priority for Don. She left, but she didn’t leave. She said she needed to get away, but she didn’t explicitly say she wanted out of the marriage. Don even suggested that they could make it work long-distance, leaving open the possibility that Megan and Don could maintain their marriage in separate coasts. Is that even what Don wants anymore? Weiner has stated that there is some ambiguity there, and that they’re not necessarily finished.
7. Is there a future for Stan and Peggy? More importantly, can Peggy have a happy emotional ending? Every career success has been met with emotional casualty. Can Peggy find someone who is not intimidated by her position? Is Stan that guy? Or could it even be Pete, since no one understands Pete like Peggy? Or is Peggy destined to become Don Draper in both her career and her personal lives? WILL SHE BE A CAT LADY FOREVER?
8. Will Sally forgive Don? This really ties into the bigger question of what kind of man Don Draper will be going forward? Has he shed the Draper identity for good? Is he determined to be himself, and not the man he’s been pretending to be for 20 years. Can he be a successul ad man as Dick Whitman? Dick Whitman is just as damaged as Don Draper in many ways, can Dick Whitman be a good father to Sally, and his sons? Will it mean a future with Betty again? Or will Don continue to make the same mistakes until the goddamn bitter end? Or could he use his ouster from Sterling Draper & Partners as an opportunity to start his own firm, or even enter a new profession?
One thing that is NOT an open question is the status of the Avon account that Joan landed (with Peggy’s assistance), as Matthew Weiner said that we’re just supposed to assume they landed that deal.