Last week when Don Draper insisted he knew Diana the waitress from somewhere, it was our cue as an audience to try to place her. Had she actually been on the show before? (No.) Was she supposed to be a surrogate Rachel Menken, or just a vague reminder of all the emotional affairs with brunettes (Midge, Rachel, Ms. Farrell, Megan, Sylvia) he’s had over the years in between anonymous blonde conquests?
But then she turned up again in this week’s “New Business”—well, maybe not so much “turned up” as “was hunted down relentlessly by Don”—and it soon became obvious who she’s supposed to remind us of. As it turns out, these two share more than just a first initial.
Like Dick Whitman before her, Diana moves from the Midwest to New York looking to escape a painful past (in her case, a marriage that has recently ended in divorce after 12 years, a daughter who passed away two years ago and, as we find out towards the end of the episode, another child she left behind in the custody of her ex-husband). That need to press forward, to reinvent and start fresh, even if it means you’re starting with nothing—that’s what Don recognized when he first met her, and once he’s aware of her backstory, he’s automatically interested in jump-starting her own Draper-like ascension, singing the praises of the city that served as the setting for his rise from lowly fur-coat salesman to multimillionaire advertising partner (he even buys her a guidebook!) and inviting her to take her pick of Megan’s old coats. (Sidenote for all the men out there: DO NOT OFFER THE WOMAN YOU’RE CURRENTLY SLEEPING WITH YOUR EX-WIFE’S CLOTHES AS A GIFT.) But Don hasn’t fully realized his own American Dream just yet, as we’re reminded by the return of that ol’ symbolic elevator, complete with an appearance from Arnold and Sylvia to recall the limbo Don spent season six suffering through. The woman he’s riding the elevator with may be different now, but he’s still riding the elevator with women, grasping at some sort of lasting human connection that to this point has eluded him. It’s a healthy reminder to Don that his old ways were flawed, that you can’t always just outrun your past; sometimes you have to make awkward small-talk with it as you wait for your floor.
Of course, he’s dealing with his recent past in more obvious ways this week, with Megan making one last trip to New York to clear the rest of her stuff out of the apartment. This is meant to close the book on their relationship, in many ways, but it’s also the most obvious example of what turns out to be a running theme in “New Business”: sexual currency. What do we “owe” our partners, and when does it stop looking like benign generosity and start resembling prostitution? We see the bad side of this with Pima Ryan, a photographer working on a campaign with Peggy and Stan who uses her sexuality to get what she wants at work. She makes out with Stan in the darkroom and makes a pass at Peggy, but when Peggy finds out about the former, she realizes Pima’s a “hustler” and declines to give her any more work. But is Megan any different from Pima? Yes and no. Don has funded her attempts at a film career for years now, and of course he made her a copywriter before that…and sure, she hits him up for $500 before her trip to New York. But their relationship was more than a simple transaction.
Marie thinks otherwise, however. She and Megan’s sister are in town to help her move her things, and while Megan just wants to get it all over with as soon as possible, Marie’s intent on packing up the entire apartment for her daughter—including all the furniture—because in her mind, Megan deserves it as payment for all the pain Don put her through. So when Megan leaves to go get lunch with Harry (more on that later), she orders the movers to load everything up, then frantically calls Roger to come over with $200 (“BRING CASH!”) when the bill is more costly than she expected. He does, and she pays him back with sexual favors because she and Roger have some sort of long-standing infatuation going on, but also because she’s a woman of her era and that’s where she’s been raised to believe her true currency lies.
Meanwhile, Megan puts on her best wig (or extensions or whatever wizardry she uses to make her hair change length within the same episode) and her billowiest sleeves to go see Harry (a person she’s openly loathed since the “Zou Bisou Bisou” incident) to ask for help with her career. She makes sure there’s wine on the table before he even sits down and turns on the charm, paying him compliments about the job he’s done helping other actresses she knows, but when Harry asks her up to his hotel room and makes it obvious what kind of payment for his services he’s looking for, she’s disgusted—not just at him, but at herself. When we see her next, she won’t even accept a cigarette from Don, telling him “I don’t want anything of yours.” In addition to making that gross casting couch proposition, Harry has reminded her that Don is the reason why she’s jobless in the first place; she quit her soap in New York and moved to California because they were supposed to move out there together. He failed to deliver on that promise, though, and as she bluntly puts it, that makes him “an aging, sloppy, selfish liar.” Don seems to agree, because he cuts her a check for a million bucks.
This, of course, is Don’s way of wiping his hands of her. He gives her enough money to last a lifetime, she gives him back Anna’s wedding ring, done and done. He knows he caused her a lot of pain, but now they’re square and he can go about moving forward, leaving her in the past as he does with almost everything else. This is where he and Diana differ. When he turns up at her apartment later that night to give her the guidebook and press onward with their relationship, he’s surprised to discover she’s not really into the whole “upward mobility” thing and wants to end it. “Can’t you see I don’t want anything?” she asks, and he counters with a comment about her dumpy apartment, saying “I know you think you deserve this.” He knows because he has perhaps entertained similar thoughts about his own mistakes in life, but Diana refuses to allow herself to pursue happiness. When she’s with Don, she’s able to forget about her daughters, and she can’t have that, so she breaks it off, and Don’s left to return alone to his apartment which, with Megan out of his life now, is both literally and figuratively completely empty. Can he fill it in these remaining five episodes?
—Marie’s decision to leave her husband and stay in New York (with Roger, maybe?) shows she’s more on the Don side of the spectrum than the Diana one, finally realizing she’s deserving of happiness. As Megan tells her sister, “She’s been very unhappy for a very long time. At least she’s doing something about it.”
—Fitting that Don starts the episode in his first ex-wife’s home, making milkshakes for his boys and gazing back at the scene of domesticity on his way out, and finishes it in his barren apartment. And the milkshakes were a nice touch—he married Megan years ago because she didn’t freak out when his kids spilled a milkshake, and now that he’s made strides towards having an actual relationship with his kids, he’s the one on shake duty.
— “Please take advantage of me.”
— “You have given her the good life.”
—Betty pursuing her own interests and going to graduate school is absolutely great, but the fact that she wants to study psychology is pretty laughable. Seems like it’s always the ones who could use a few sessions with a psychologist themselves who wind up going into the field. Hopefully she’ll wind up understanding herself a little bit better.
—Between Pima this week and her confrontation with Joan last week, so far it seems like the theme of this half-season is “Peggy is uncomfortable with powerful women who have used their sexuality to get ahead.”