At the close of last night’s Mad Men Season 6 premiere, Don Draper reveals his New Year’s resolution to his latest mistress, saying “I want to stop doing this.” Sylvia, Dr. Rosen’s wife, says she knew that to be the case. However, Don’s use of pronouns, and absence of therapy sessions, paves the way for fun viewer speculation as to what exactly it is he wants to stop doing. Better still, there can be discussion about why he, apparently, lowers himself, and periodically feels twinges of guilt.
Taking a Freudian approach, delving into Don’s sketchy, but unfortunately turbulent backstory is a necessity. The women in Don’s life have been disappointing him, literally, throughout his entire life. His mother, a prostitute, died while giving birth to him. It’s difficult then to lay blame for Don’s issues at his mother’s feet because she certainly didn’t choose to abandon him; however, it was repeated to him on many occasions throughout his childhood that he was a “whore child,” so, even from beyond the grave, his mother’s character was a nuisance to him. Abigail, Don’s stepmother, must not have been so wonderful to Don either because when Don is informed of her death from stomach cancer, he says to his half brother, the bearer of that news, “Good.” Therefore, by the time he was a teenager and joined the army, Don’s positive experiences with women were likely minimal, if there were any at all.
In Betty, he found someone as childish as she is beautiful and, for a time at least, he could control her. After years of infidelity, Don finally proves to be untrustworthy when Betty learns of Don’s prior identity as Dick Whitman. The staggering truth that Don is a man Betty doesn’t know-a reality that any woman only minutely more aware than Betty is would have seen years prior-is finally too much for her to bear, and she files for divorce. Rapidly, in Don’s eyes, the best thing about Betty, her immaturity, becomes the most infuriating aspect of her personality as he tries to navigate his new life as a single father. Betty uses their children to control Don, making it increasingly difficult for him to be an effective, even loving parent. In short, Betty becomes an incredible irritant to Don, just like his mother and stepmother.
Don tells Peggy towards the close of Season 5, “You help people, and then they move on.” This was soon after Peggy had left Don’s firm where, under his tutelage, she’d learned all her advertising trade tricks, but, at that point, Don was really referencing his wife, Megan, and not really trying to impose guilt upon Peggy. He checks himself and quickly insists to Peggy that he is indeed proud of her achievements. In the case of Megan, Don was feeling duped because in his former secretary, he thought he’d found another woman he could control. But when she gets the acting bug in her, he’s combative and tries to restrict her pursuits. Turning over a new leaf, Don gives in, hopeful that he can still find comfort in someone so independent, and he lands her the gig in a commercial that his very own firm was producing.
To Megan’s credit, she looks intent on balancing her career commitments with those that come with being in a marriage. For instance, she appears genuinely upset that she can’t attend Roger’s mother’s funeral, an event that Don, as a partner of Roger’s, would most certainly have to attend. Don says he doesn’t mind, which also comes after he seemingly restrains some internal frustration at her newfound notoriety during their Hawaiian trip. So, despite Megan’s best efforts to be a good wife, Don’s anxious anyway.
Don cheats on Megan because he expected her to be a disappointment to him. Now, because she is doing her own thing as opposed to sitting at home waiting for him to arrive for dinner, Don’s bailing. His current swing into infidelity is the result of a self-fulfilling prophecy. All of the women in his life, his mother, step mother, Betty, and, though they weren’t a couple, even Peggy, have been a source of some varying degree of angst for Don. It’s virtually impossible then for Megan to keep Don close, for Don’s just been waiting for a reason to leave her all along.
Don’s “first wife,” Anna, is the lone exception. They had “an understanding” and “it wasn’t romantic,” he tells Sally in Season 5. Anna was nice enough to allow Dick Whitman to go on living as Donald Draper and, when he asked her, nice enough to divorce him too. Don struggled with her untimely death and now only speaks fondly of her whenever he must to the few people, all women, in his life who even know of Anna’s existence. Anna could be an illustration that there is a section of Don’s character willing to turn itself completely over to one woman. However, it might already be occupied by Anna, a dead woman whose entire presence in Don’s life, as someone who allowed Don to do whatever the hell he wanted, was a positive one.
So, as Don reads Dante’s book about “you know where,” to quote Roger, he’s pausing to actually reflect on his sinful actions. Don doesn’t just want to stop sleeping around, he wants to thwart his reemerging tendency to sabotage relationships with women. Perhaps it’s because Megan is proving to be simply a better woman than Betty as she makes a concerted effort to not let Don down, despite wanting to achieve her own personal goals. Or it could be that Don has matured and finally grown tired of the intensity that comes with cheating, the very thing that for years could have provided him with a thrilling rush of excitement. Whatever the reason for Don’s potential enlightenment, the root cause of his behavior goes back quite a ways, and it’s a bit unsettling to think Megan, through no fault of her own, could experience some painful days if Don can’t figure this all out.