Don Draper’s final look in Mad Men season 5’s finale was the ultimate cliffhanger. The look, executed masterfully by Jon Hamm, left us wondering what his trajectory now is.

I see Don as a traditional man who is trying to adjust, and embrace, modern society. We already know the ways in which he’s comfortable with traditional gender roles and other conventions (smoking, drinking at work.) But we can’t downplay the fact that he hired a black secretary, breaking tradition. He got divorced and remarried, also breaking tradition. In fact, even employing (or promoting) Peggy way back when was a break from tradition. Sometimes he may have resented her, but he was willing to cross that line. Because, I believe, Don is trying to be an optimist. He believes in the future and he believes he can have a part in it. But what happens when he backslides into past behaviors?

We’ve already seen Don struggle with the ghosts (or phantoms) of his past and how he used to consider infidelity both a right and a pleasure of his married life. But with his new marriage, he’s been determined not to be unfaithful. And part of that has probably been selfish. With a new wife, he figures he should be content and happy with her – at least for a while. What does it say about him if he can’t enjoy it at all?

He probably also knows how much his cheating hurt Betty, and he resolved himself to treat Megan better. And he has. He’s never controlled Megan the way he controlled Betty. In part, I believe, because Megan just wouldn’t have it. Megan is a modern woman. This is why Don and Megan made so much sense.

But now, instead of trying to control everything, Don has given up what he feels like doing in order to obey Megan’s wishes. He didn’t want her to audition for a commercial with his company or pull strings for it (his pride, his pride!) to happen. And he wasn’t going to. But then he heard Megan’s mother, so resolute in her defeatist ideas about Megan’s dreams… and I think he immediately realized that if he wasn’t going to take care of her, no one else was. He wanted to make her happy. And he rejected the idea that Megan’s dreams couldn’t come true. Suddenly, he was on her side.

And we don’t know how much influence he had, but he must have taken a step that helped land Megan the gig. And there she was, in technicolor glory – in a true fairytale. And she was so happy. She was glowing.

But Don hated it. He removed himself from it. He had done something unselfish, and now he regret it. He’d made Megan happy at his expense. And he isn’t used to that. Megan’s happiness wasn’t enough for him.

So we leave Mad Men’s fifth season with Don feeling a barrier in his marriage. Can he contort to allow for a more equal marriage? Or does he feel he’s owed those old luxuries of infidelity? Is he miserable? And what would that misery help excuse himself of his marital bonds once more? We have to ask ourselves, not just whether Don will ever stay happy, but if he can be miserable without acting out like a child about it. But if he just shut up and played like a good boy, would we really want to watch him?

No. The truth is, we love us a rebel.

Mad Men “The Phantom” Review. Photo: AMC