In a season that contemplated some particularly dark ideas, Don's deluded, love-drunk smile, which he offered repeatedly in the Season Four finale, "Tomorrowland," was the darkest of all.
Nobody knows what's wrong with themselves, but everyone else can see it right away.
-- Stephanie (Caity Lotz)
It's not often that a TV series can elicit that genuinely sick feeling in the pit of your stomach, the one you get when you watch someone you care about make a cataclysmic mistake. In the case of Mad Men, Don Draper (Jon Hamm) rationalized that choice as a new beginning determined by “fate.” And that rang as false and desperate and very, very sad in all of the ways that Don himself usually deplores. In a season that contemplated some particularly dark ideas, Don's deluded, love-drunk smile, which he offered repeatedly in the Season Four finale, "Tomorrowland," was the darkest of all.
While Don and Megan inexplicably fell in love, plenty of development and dénouement happened in the periphery, tying into this season's theme of self-fulfillment leading to self-understanding. Almost. Peggy (Elizabeth Moss) landed her first big account, using everything that Don ever taught her to wow Topaz pantyhose. Joan (Christina Hendricks) didn’t have that abortion after all, which means that she’ll be doing some fuzzy math when her husband returns from Vietnam (if he returns). And Don’s ex-wife Betty (January Jones) endeavored her own fresh start by firing her nanny in a regressive, jealous rage. Her only redemptive moment was the tender, easy drink she and Don shared from a plastic cup in their now empty house.
Let's just get it out there: for someone so smart, Don is incredibly stupid. He's become the cliché he despises (remember his disgust at Roger Sterling [John Slattery]?), in order to avoid reconciling Don with Dick Whitman, his real identity -- the one he left behind in the Korean War. As this season launched into a lurching push-pull between Don wanting to come clean and frantically trying to continue posing, his impulse to marry Megan, a girl who knows about as little about him as he does about her, suggested that he won't be owning up anytime soon.
Talk about two steps back. Three episodes ago, Don, physically racked with anxiety and guilt, confessed to his lover Faye (Cara Buono) that he had assumed Don Draper's identity. She listened quietly. The ease with which he spoke and the burden he felt lifted left them altered, seemingly for the better. It looked as though Don might understand the kind of honesty required in having a grown-up, fulfilling relationship. And surely Faye met all those superficial requirements Don had: smart, blond, caring, and lamp-rattlingly good in bed. What more did Don want? He wanted... well... he wanted less.
The more post-confession time Don spent with Faye, the more she pushed him towards coming to terms with his past in order to secure a happy future. As excellent as that advice sounded, Don didn't want to think about his past, and the more Faye brought it up, however lovingly and necessarily, the more her odds of remaining in Don's life dwindled. As he broke the news of his engagement to Megan to Faye, she heard him out with wit and grace, then fired one sure-shot arrow before she hung up the phone: "I hope she knows you only like beginnings." Ouch.
Don does like a few other things. He likes his children (who might be understood as “beginnings,” too, at least as long as they stay young). And when he saw how well Megan got along with them ("Maria von Trapp," he called her), he was moved to adore her... more. (Could it be so simple, and so complicated, that deep down, he really just wants a Mommy?) When Sally (Kiernan Shipka) and Bobby (Jared Gilmore) bickered at a restaurant, toppling a milkshake, Megan’s handling of the situation was so completely opposite of the shouting, blaming and guilting the Draper kids and Don have come to expect from Betty that they were all rather stunned. “It’s just a milkshake,” Megan said coolly. Yes, it was just a milkshake, we thought. But it's not always going to be just a milkshake.
But while Megan may symbolize to Don the very opposite of Betty, she’s really not all that dissimilar. Both knew little of the man they married, and both had clear goals they needed Don to help them achieve (Betty aspired to be an idyllic suburban homemaker; Megan, an upwardly mobile career gal). That Don didn't see this new beginning was only his old cycle beginning again made the couple's longing looks and heartfelt moments more painful and sad than any this season had rendered. We like beginnings too, which is why we watch TV series that begin again and again. But we also understood: when Don said, “You make me feel like myself, but who I always wanted to be,” he wasn't able to acknowledge the paradox. We, of course, could see it right away.