IF YOU AREN'T CAUGHT UP ON MAD MEN, FIX YOUR PRIORITIES AND GET BACK TO US LATER.
Pete Campbell makes a woman give up her seat for him when he shows up to a meeting late. He spends the entire episode (which aired on Mother's Day, mind you) taking advantage of his mother's Alzheimers and he threatens Clara when Don and Chaough go upstate without him. "My mother can go to hell and Teddy Chaough can fly her there," he yells. Still, he's only the second-most detestable character because Don Draper's inferiority complex came out to play this week. And it takes a LOT to cast a scumbag shadow over the vile Pete Campbell.
The merger is in full swing and, predictably, Joan has a clipboard and all of the knowledge (but, none of the respect) that comes with it. Ginsberg and the rest of the creatives are stuck sharing an office and arguing over a margarine campaign. Don misses the creative meeting and, when Chaough chides him for showing up 40 minutes late, convinces his new associate to drink and tackle the margarine campaign together. When Peggy chastises Don for luring Chaough into a daytime stupor, she reveals that she's so vain that she probably thinks the merger's about her. Don's retort, about having her back in his office complaining, was mean-spirited, but looked like high praise compared to the sadomasochistic song and dance going on in room 503 of the Sherry-Netherland.
If we've seen Don go on power trips before, then "Man With a Plan" is a sabbatical of epic proportions. From the moment Don hears the Rosens arguing in the episode's opening scene, we can feel his wheels turn as power swings in his favor in his relationship with Sylvia. Find my shoes. Get undressed. Get in bed. Don't go anywhere. Don't answer the phone. Wear this. Don't ask any questions. Get undressed. The "king and peasant" routine that he pulls from his hotel throne and his "you exist in this room for my pleasure" line were a vivid examples of Don's entire issue with women.
When he and Sylvia are laying in bed, she asks him what she's supposed to do next. He tells her that he's going upstate and he expects her to be ready for him when he gets back. "I can do that standing on my head," Sylvia replies. And that's exactly the point. Don's gone through life enchanting capable women and reducing them to exotic pets. Betty was a model when she met Don. He turned her into a petty, snobbish, suburban housewife. Megan was shining as a copywriter and, though she's acting now, she's going out of her way to sexually objectify herself for his amusement and asking the staff to write her off so that she can go away with him. Sylvia is just the first literal manifestation we've seen of Don's addiction. She got a taste for his special brand of bulls***. The Don Draper giveth, the Don Draper taketh away. The Don Draper will end up forever alone.
When they're flying upstate, Chaough and Don are discussing their upcoming meeting.
"No matter what I say, you're the guy who flew us up here in his own plane," Don remarks. The line is a tell. Don Draper is really just Dick Whitman's meticulously honed poker face. It's why Teddy Chaough can't seem to get a read on him.
"He's mysterious," Chaough said, earlier in the episode. "And I can't tell if he's putting it on. He doesn't talk for long stretches and then he's incredibly eloquent."
As the rest of the characters on Mad Men struggle to play a hand with Don Draper, Dick Whitman is bluffing all over the place just to make himself feel like an adequate man. It's why he tells Sylvia not to talk about her husband. It's why he needs her to to consistantly remind him that she needs him. It's why, no matter what he says, he'll never feel like the guy who flew up there in his own plane.
His pathetic, "Please?" is too ironic, too late to save the tryst with his downstairs neighbor. Just as she wore out her welcome as his muse, he's worn out his welcome as her savior. It's the first time he's asked her for anything and, by this point, she's too ashamed to give him any more than she already has.