Something didn’t sit right with me for the duration of this episode; I felt disoriented throughout all of it, as the storyline with Don and Diana the waitress from last week surprisingly continued, with Don spending some shoe leather on how to find her at her new job and then striking up a courtship.
They didn’t seem to have anything in common at first other than a tendency to skip right to dessert (so to speak) without a lot of chit-chat, so I was puzzled by this relationship that they both seemed to be treating as important right away. But then it hit me, when Diana spoke of her lost daughter and abandoned home in Wisconsin, that Diana is like a female Don: she cut and run when things got difficult and is trying to start over in New York. But I still don’t really get what Don is after here.
Slate’s Hanna Rosin is on the same page:
Diana, the itinerant waitress from Racine, Wisconsin, is a female variation of Dick Whitman: on the run, lying, trying to manage her secrets but never really escaping them. I was wondering why Don insisted on seeing her apartment. He had to know it would be a dump, and his presence there would cause her shame. But he was obviously looking for something. His apartment—like something out of Architectural Digest, she said—was like a stage set for her New York fantasies. But he didn’t want an actress. He wanted someone who would feel a “twinge” in her heart, and I think, but I’m not sure yet—he wanted someone he could save. I’m not sure I buy the Don/Diana relationship, or if I like the air of Raymond Carver realist unreality that hangs over them. But it did produce some of the best dialogue of the episode. The conversation in bed where they seem to be acting out a commercial for Avon—“You smell incredible. What is that?” That scene felt like a replay of Don’s dream last week about Rachel in the mink commercial. (“You’re not just smooth. You’re Wilkinson smooth.”) And the soap opera vibe brought on by Diana’s story about having left her little girl behind, which was then punctured by a Groucho one-liner: “You should go,” she says. And he answers: “But this is my house.”
Salon’s Sonia Sariya focuses on the episode’s other main character, Don’s estranged second wife Megan:
My guess is that because Jessica Paré’s character took up so much space in this episode, she won’t be coming back. And her send-off, much like her marriage with Don, is an episode of much glorious revving of engines but never finding a way to take flight. Partly that’s because the episode spends so much time with Megan herself, and Megan Draper nee Calvet has been, by design, a very thinly sketched character. At first she was just that one woman in the test group who washed her face with cold water; then she was the secretary with a sense of humor; then she was Don’s fiancée who didn’t flinch at a spilled drink. She was constantly being presented as an alternative to someone else—usually another woman. And unlike Don’s previous wife Betty, we didn’t eventually come to understand her character. (The show did, at times, offer more insight into her character, but it was not the level of examination directed at Peggy, Betty, or Joan, to name some of the show’s strongest female characters.) “New Business” is, in some ways, rubbing the fact that we never really knew Megan in our faces. Megan breezes into New York with not just her movers but also her mother, Marie (Julia Ormond) and a previously unheard of sister, Marie-France (Kim Bubbs). Both are unhappily married, but loath to admit it. Megan’s divorce is, according to both of them, doing something terrible to their family. It’s not an uninteresting storyline, but it comes out of nowhere, reminding the viewer just how little we know about Megan’s interiority, her upbringing, her relationship to her Catholicism. Diana (Elizabeth Reaser), the waitress that Don has a brief, sad fling with this week, reveals more about her particular loneliness in one episode than we ever learned about Megan in her multiple seasons on the show.
Alan Sepinwall was frustrated by the episode:
The craft of the show has been so strong most of the time that I haven’t been particularly bothered by Don’s inability to grow. “New Business,” though, was an episode so frustrating — and, with few exceptions, dull — that I could for once see that point of view. Now, “New Business” was an episode specifically about how Don — like Roger, Pete, Harry and others — is trapped in a cycle of personal weakness and failure, and about Don’s acute desire to escape that cycle. (Contrary to the title, he spends much of the hour dealing with old business, and failing to land the new relationship he wants.) He begins the episode looking at the first family he lost, and feeling an acute pain at realizing how well they’ve done without him. As soon as he gets home, he’s greeted by a phone call from Rightfully Bitter Ex-Wife #2, and even when he gets Diana to come back to his apartment a second time, they wind up in the elevator with Arnie and Sylvia Rosen. As he did before with Megan, Don decides that a woman he barely knows is the solution to all his problems. But Diana isn’t nearly as simple as Megan was — or, rather, as Megan seemed at the time. She lost one child to the flu, and ran away from the other, and while Don Draper may be the man in New York best qualified to appreciate someone’s need to run away from their problems and/or family, she’s not buying whatever he’s offering to her when he says he’s “ready.”
Grantland’s Molly Lambert draws an interesting line from Betty to Megan to Diana:
No, that wasn’t a dream: Betty is going to go to school to be a shrink! She’s found her true calling. People tell her things! I love it whenever Betty reminds Don that she’s not as dumb as he always made her out to be. Betty will learn all kinds of things when she gets her master’s in psychology. The whole Oedipus complex thing might interest her in particular, because man, does Don Draper ever have one. It’s not that Don seeks out women who are, like his mother — who died giving birth to him — prostitutes. He just has a thing for broads who were dealt a bad hand. He likes women who suffer from depression, but not the sort of depression that plagues Betty and Megan, who might have been sunnily happy people had he not involved himself in their lives. He likes women who were born sad, on whom no good circumstances or outside stabilizing force can ever bestow lasting happiness. Diana begs Don not to get involved in her life, over and over, but that’s like a siren song to him. Don loves a woman he has to talk into things. He’s drawn to desperate, low-lit places, physical and psychological.
And Tom and Lorenzo call the dalliance with Diana Don’s saddest move yet:
Don, having dealt with his former marriage through the writing of a check, rather pathetically (and in typical Don fashion, completely blind to the other person’s state of mind) declares to walking sadface Diana that he’s “ready” for her. The only thing that differentiates this completely insane and desperate declaration of love from the similarly feverish one that greeted Megan years ago after a weekend spent babysitting his kids, is that Don knows even less about Diana than he did about Megan. And at least in the case of the latter, she was charming and bright and was able to appear interested and affectionate toward his children. Diana is almost hilarious in her moroseness and the heavy air of tragedy that hangs over her. A human Eeyore in a waitress cap. Megan was the happy Maria Von Trapp clone that could teach his children songs and wipe up spilled milkshakes with aplomb. Diana is the mother of one dead child and one abandoned child. That he honestly thought he could find happiness with this sadness generator is perhaps one of the most pathetic things about Don and his state of mind right now. At least after his first marriage he paid lip service to the idea of trying to figure out what kind of man he wants to be and what kind of life he wanted. He wound up running away from those questions and revelations (in the form of Faye Miller) and straight into Megan’s arms. It was a means of avoiding dealing with himself. Now he’s so degraded that he’s skipped past even the self-examination part and headed straight toward the avoidance. “It’s 3 in the morning.” he says to Diana. “You know why you’re here. Do you want a drink or not?” That’s pretty much where Don is now.