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What makes Don Draper dashing is the suit, especially. And the hat, the jaw, the hair, the voice, the way he fixes his attention on a woman. But what makes Don Draper seductive as a person and not just a sexual partner is that he is perpetually a whisper away from being a better man. If he were just dashing, he would be harmless; it's that he's seductive that makes him dangerous. It's how close he seems to becoming better that makes him toxic.
Don's biography is defined by his conspicuous reinvention, driven during the 1960s by his desire to move in a phototropic arc from a steel-and-glass Manhattan toward a literal and metaphorical West. But what he winds up making are lazy, meandering circles in which he repeats the cycle of feeling damaged, causing damage, and feeling more damaged as a result.
There is perhaps no greater lie embedded in our grand cultural self-improvement fable than the idea that feeling bad about the pain you cause is a reliable and important step toward not causing it anymore. Mad Men has always been straightforward on this point. Don always feels bad. Don felt bad about cheating on Betty, just as he feels bad about cheating on Megan. He has looked wrecked over and over. He has cried. He has sweated. There are no firsts in his despair.
And when he married Megan, there was a popular theory that in spite of how silly their marriage appeared, this was a woman who truly loved him, who truly accepted and knew him. A woman on whom he would perhaps maybe not cheat. There has been suspicion in many corners that Betty caused his cheating herself by being so icy and brittle. Betty was a cold and Megan was a warm, and with Megan, he maybe wouldn't cheat.
But his cheating didn't get better; it got worse. He didn't just cheat on Megan, he humiliated her, twice, by having sex with one of what seem to be her few friends and then having sex with his ex-wife — his ex-wife about whom he has complained to Megan bitterly, resentfully, ceaselessly. His ex-wife whose children Megan has cared for while he largely behaved indifferently. It would have been difficult for him to find two ways to be unfaithful to Megan that would more emphatically announce disdain for her, and yet he still believed to the end that the answer to everything was to grab her, take her, get her and go, go, go to California, get out of here. Because in California, it's going to be better. California is Don's "someday." Not just "someday," though — someday soon. He's just about to learn something, you can tell. Always.
Sunday night's season finale was about Don having yet another breakthrough. Don loves breakthroughs. He loves them so much that he has them all the time. Most dysfunctional people are chasing a feeling, and the feeling Don chases is that he's right there, that he's turning the corner. That's how he acted after his brother committed suicide. It's how he acted when Betty kicked him out. It's how he acted when he went back and visited Anna. And when Betty got pregnant. And when he came clean with Betty. (Especially then.) And when he consented to the divorce. And when Anna died. (Remember when he was journaling?) And when he took out the smoking ad, married Megan, lost Peggy.
This is rock bottom. Now I get it.
Well, now they've given him an involuntary leave from Sterling Cooper & Partners — which, if it's anything like Peggy's departure or Joan's departure, will seem like a hugely important character moment and then be quickly and neatly undone. Given that Sally has been shipped off to school and Megan seems to be ready to leave, the idea that this is a real break between Don and the firm is awfully difficult to swallow, since he's unlikely to spend the last entire season of the show with Betty, who would be just about the only one left. Sure, he had a bad moment in a meeting (not his first) and spilled his guts about having had a difficult childhood. But remember, Bert and Pete already know about his past. Having people at SCP in on his secrets is not new at all. Telling the clients is, maybe.
As for the moment of truth with the kids that was intended to carry the weight of the closing sequence, all he told them, effectively, was that he grew up in poverty. Does that mean he intends to tell his kids that he's a fraud? Does he intend to let them in any further than that? Does he intend to either come clean with Megan or leave her so that the enormous pressure he's placed on Sally, which sent her fleeing to boarding school, will be lifted?
Is all this sweaty, puffy, pale misery going anywhere?
Mad Men has been brutally fair about Don, about sending a single message: he doesn't learn. He can't. He will meet kindness with cruelty, he will think of himself and not others, and he will never stop believing that just out of his reach is his better, kinder, greater self. Any day now.
Perhaps ironically, what made the season finale unsatisfying is the show's integrity. Don goes in circles; this is how it is. It is sad, but it is permanent. And they've told that story beautifully, heartbreakingly, and artfully. The most honest and right decision in Mad Men history was Peggy leaving, because she knew it. She knew he'd never change and would continue taking advantage of her. And by not changing, she knew he'd keep breaking her heart, so she left. Not maliciously, not even all that angrily — she just left. Because it was over.
The agonizing repetitiveness of Don Draper's self-indulgent self-destruction is a story Mad Men has told, and told well, but it's a story about which, almost by definition, there is nowhere to go now. It's not plausible he will leave the agency from a producing-the-show standpoint; it's not plausible he will change from a story standpoint.
That doesn't mean the show has nowhere to go. This season began with such a new and interesting dynamic for Peggy, only to suck her back down into the pit of Don's mistreatment, so it's hard to be confident that her stepping into Don's office/shoes will stick when he inevitably returns. But it could; there could be some story for her other than "Peggy's personal life is terrible, but she's moving up at work." The ramifications of the partners pimping out Joan were touched on this season, but only lightly; there's a ton of story there, too.
As for Don, the best scenes he played this season were with Betty. That is the one relationship in which he now seems capable of genuineness. Early in the show, she was the wife he dismissively kept in the dark, dolled up like a house decoration. Now, she's his confidante. She knows his secrets. She can explain him to himself in a way that makes sense to him. She is the one person who truly knows him and still cares about him. She has more reason than anyone to think he's a monster, but she's not the one who said so. Their encounter this season was probably the first time they've had sex out of genuine affection not tainted by lying. That relationship is interesting.
But the idea of a Mad Men episode having heft because Don makes progress by hitting bottom and making a gesture that suggests he's been broken by his demons and is ready to search for happiness? That's an illusion, always. It's always been one, and it will always be one. He is this person, for better or worse, selfish and dishonest, obsessed with his own hurt. There are lots of ways to tell that story, but to believe in his growth as a person is to be seduced by his toxicity.