The appearance of the enigmatic waitress Diana in the Mad Men universe and Don Draper’s life in episodes eight and nine of this final season seems to have caused a lot of viewer consternation.
Two distinct elements are in play here.
First, for some viewers this feels like “Here we go again!” with Don not just falling back into old patterns (that’s giving him credit for actually stopping) but merely perpetuating them, rote, a man who cannot resist the next woman, the next chance at happiness or just something different.
Secondly, Diana (Elizabeth Reaser) appeared in the second half of the final season and so far has been a fairly large presence. What that does for many viewers is create a sense of panic: There are now only five episodes left ever and who the hell is this new character and what is she doing taking screen time away from the story resolution of so many beloved Mad Men characters?!
Taken together — Don doing the same old thing all over again, and with a woman who, by the way, isn’t exactly lighting up the screen with her charm and personality — these elements create fear that Diana is a pointless detour at best and a frustrating waste of time at worst. It’s making some viewers check their watch repeatedly as time runs out on this brilliant series. They want some kind of closure for Peggy, Roger, Pete, Joan and on down the line. Clogging up the hour with Diana is making them antsy and grumpy.
While this is all understandable, Mad Men creator Matt Weiner should at least be given the benefit of the doubt at this point — he knows what he’s doing and, more importantly, what he wants — and perhaps some people have missed how different Diana is from almost all of the other women Don has rushed to in this pattern of repeating his mistakes (which is, by the way, one of Weiner’s stronger tenets — that people don’t really change; you may ultimately find that boring, but it’s a consistent notion of his about the human condition).
As someone who deeply and passionately hated the Sylvia storyline from season six — a diversion partly necessitated by the contract Weiner and the show have with AMC (there was always going to be a seventh season given the contract language, but structurally it almost guaranteed that season six was going to be more filler than ending) — I don’t think there’s any connection between Sylvia and Diana.
Don pursuing Sylvia was disappointing and frustrating because it was the epitome of been-there-done-that with Don and arguably didn’t have a believable reason for coming to fruition (if you buy into the idea that Don needs a reason for screwing around and screwing up his life).
If you tumble back through all of Don’s women to his most egregious affairs — the ones that changed the course of the series — it was clear from the beginning that Betty was never the right fit. She was always the fantasy wife that a man living a lie like Dick Whitman would choose to convince himself he was getting everything he wanted, or everything the cliches of life told him he should want. We know now that Rachel may have been the love of his life (after initially being just an escape from Betty). She was, in the parlance of this season, “the life not lived.” (Anna Draper was probably the only woman who ever “knew” Dick/Don and she’s arguably the one woman — Peggy a trailing second — to whom Don has ever been vulnerably close).
After a flurry of women and bad decisions, it wasn’t until season four with Faye that Don appeared to be getting his act together by going out with someone closer to his age, who was smart and a challenge for him. But a pattern emerged. In season one, Don — in full panic after Pete discovered who he really was — runs to Rachel and is willing to leave Betty (and the kids!) to start a new life with her. But, being a smart, challenging woman herself, Rachel realizes Don is just running from his problems and cuts him loose. In season four, when a blunder from Megan, then his secretary, essentially re-creates and revives the hidden-identity issue, Don wants to run away again. This time Faye is there but advises him to come clean (something he can’t and won’t do). She wants Don to own up and man up — to be an adult. Half of his mind is made up right then that Faye is not his answer because, in his second-biggest decision since racing to Rachel, the answer he’s given is one he won’t accept. Unmoored, Don witnesses Megan with his kids being the sweet, natural mother that A) he never had and B) Betty never was and C) Faye couldn’t be, and it sets the stage for the surprise (and somewhat shocking) marriage proposal to Megan.
At least in season five the deterioration of Don and Megan’s marriage is better explained — the age gap, her career motivations, his relentless unhappiness with life itself. (The season actually deftly hid Don’s slow arc of “Is that all there is?” with a new wife and increased success by juxtaposing it with Pete’s more painful and dramatic marital unraveling).
So if viewers have anxiety over the appearance of Diana and her role in Don’s life, blame season six and its ill-advised Sylvia storyline and the slower, more annoying bi-coastal disillusionment Don undergoes with Megan. The combination was more drone and drag than ever before (though arguably season six had some pretty spectacular random episodes even if the season as a whole was weak).
But yes, season six was when even the less antsy fans, the ones who understand that Mad Men is in many ways a claustrophobic, interior character study of one flawed man, became disgruntled at the repetition that many now see as, well, repeating with Diana.
However, we’ve had a much different and more soberly aware Don in this seventh and final season. Nobody knows how it will end or what the fates of the various characters will be. But at least Weiner planted the notion that even if Don’s continued existential crisis doesn’t lead to enlightenment or happiness, it might still lead to Don realizing that whatever he has now may not be perfect, as he imagined so long ago, but it could be enough. And that’s why Diana’s arrival is important at this crucial stage of the series.
With the season split into two seven-episode halves, we learned at the end of the first seven that Don was creatively back, but that he and Megan were done. As this last batch kicks off in 1970, Don and most of the other major players are “filthy rich” — the pursuit of success is less important to them, and the actual advertising and workplace scenarios have taken a back seat. This is the twilight of Don’s career — he can even write Megan a million-dollar check to settle the divorce, give her the life of happiness that he couldn’t as a husband and, importantly for Don, just be done with it (no more fighting; no more talking).
With Megan in California and effectively an “ex,” Don is free to enjoy the Swinging ’70s right out of the gate. The first episode shows him happy, dating, screwing, etc. — he had calls in from four women as if to suggest that he’s just a slightly younger version of Roger, salving his unhappiness with booze and women.
Until Rachel dies.
Until he realizes that even Betty and Henry (and the boys) seem happy.
It’s becoming clear that “the life not lived” is going to haunt him. This remains entirely consistent with the main theme of Mad Men.
And then Don meets Diana, whom he thinks he knows — not just from somewhere, but somehow knows, truly and deeply. The second-half premiere introduces Diana in a very odd, almost dream-like way. Last week’s episode diluted the semi-fugue-state feel but kept Don interested in Diana — just not how many people seem to think.
Diana is different from the stewardess and the model and whoever else might be calling Don every night. Post-Rachel’s-death, he’s a changed man — which is both a consistent development for the series and a significant plot point that Weiner is trying to spotlight in this last rush to the end. As a character, Don has to wake up to the sum of his life experiences to this point. Rachel’s death is an epiphany and Diana’s arrival is … something else.
I’m not exactly sure what, and with five episodes left who could be? But I do know this — she’s not Sylvia. She’s not the stewardess who spilled all that ominous blood-red wine over Don’s carpet. Diana isn’t a conquest. There is no lust at all in this connection between her and Don. She’s not filling a need for happiness or replacing his mother or being swapped out for Betty. If viewers are thinking, “Oh, not again,” they should instead be thinking, “Oh, what the hell is this?”
Because it’s different. And it’s significant to Don Draper’s concluding storyline.
We could certainly look at Diana as a version of Don himself. That’s why he thinks he knows her. She’s him. Diana is running away from her husband and family. In the last episode, we learned that one of Diana’s daughters died and it was a situation so deeply sad and unsettling for her that she also abandoned her surviving daughter (and husband). Like Don, she chose flight.
She’s punishing herself for her choices, moving to New York where she knows no one and also wants to know no one. She’s emotionally shut down, calculatingly not living life. Now that she’s met Don, his fascination with her (again, no lust even though there’s sex involved) has sparked something in her heart that she didn’t want — a flicker of happiness. At the end of the episode, she said she was likely headed out of New York and off to San Francisco — because she doesn’t want to allow herself to feel that twinge again. So she’s running away.
We don’t know how long Diana will be around — maybe she’s gone for good. Maybe she was just meant to pass through Don’s life as a mirror-reflection of the kind of person he was not long ago. It’s pretty clear though that Don was attracted to Diana’s hurt, to her deep sadness (I like that she’s a brunette who looks a little bit like Midge, Rosemarie DeWitt‘s character, and little bit like Rachel). What’s far less clear is Don’s motivation for wanting to be with Diana. I don’t think he paid off Megan just to clear the path for Diana. But he did announce that he was ready to commit — that, too, is a Draperism we’ve heard before. Don has regularly been all-in without fully thinking out the consequences. It’s how you live a life of temporary joy and then abiding unhappiness. But this time, what Diana represents is far less clear than what Rachel and Megan represented.
Maybe Don’s on the other side now — he’s the one who can help out a lost soul. He’s what he wanted from Rachel, what he got from Megan. Maybe Don’s odd connection to Diana’s pain is his way of finding that part of himself that’s missing — the hole that the marriages and the money and the women and the booze didn’t fill. Maybe being some kind of stabilizing force for a wayward soul is Don’s final redemption, an act that gives him meaning and purpose.
Only more episodes will provide the answers. But this is where we are in the story, and it’s a theory that would at least be consistent with his existential drift.
And lastly, before this next episode, a quick thought on viewer frustration with Diana representing a detour that will delay the storyline (and closure) they so desperately want First, don’t think of Diana as some last-minute add-on. As the visionary creator who has guided Mad Men this impressively and this far, Weiner is introducing this character because she’s a connecting rod to his story about Don — there’s meaning to what Diana represents to Don. Whatever she turns out to be, Weiner put considerable thought into it. Give the man credit for that at least. She’s not a creation he’s throwing into the final seven episodes as a diversion or a place-holder (like Sylvia was). Diana matters somehow.
And if people are worried that Peggy, Roger, Pete, Joan and everybody else’s story won’t get enough attention, consider this: Weiner never promised that it would end neatly and with a definitive notion about what happens to everyone. His Mad Men world has always embraced the philosophies of existence, and none of those are very tidy.