"Volare" is playing in Roger's office, where Don sits with Eleanor's legs across his lap, totally not feeling this whole sordid scene. It's really refreshing to see, for once, somebody on this show be like, "Wait, I'm stuck in gender Viet Nam without an exit strategy! Gross! There is not really a compelling need for me to fuck a twenty-year-old in order to prove my future earning potential to Roger Sterling! 1960! I am so over you!" Not getting the obvious hints that he's not that into her, Eleanor -- whom you only thought was kind of demeaning herself here -- tries to kiss him, and he vaguely kisses her back. She finally hauls her legs off Don, and he makes to leave for the, what, eighth time, and then HOLY HELL. That Goddamned Roger Sterling comes into the room riding Mirabelle like a pony, in her underwear, laughing. And her back is bowing under him, and Don's about to barf, and both of them are laughing until they are rolling around in the floor, but I don't think either of them really mean it either. I don't think either of them find it very funny, I mean. Here's what I think: I think 1960 is gender Viet Nam and unless you really check in with yourself, you could end up almost anywhere at all, and I think that any time the Marquis De Sade shit starts, somebody's not being honest. And I think that Roger is like a toddler who actually really wants his limits defined for him, but nobody will do it because he's too rich and too powerful, and women can't do it because he's very, very beautiful in addition to those things, so he has to go to these grotesque extremes -- while also having his power illustrated for him by the fact that not one person is supplying the totally obvious fact that you do not ride naked ladies around like ponies, and fucking everybody knows that, 1960 or not. So that's the positive reinforcement as well: nobody can tell Roger Sterling no, so it's kind of like everybody is telling him yes. It makes me sad for him. I love Roger Sterling very much.
Don actually manages to make it out of the room this time, and Eleanor follows him -- not to continue her glacial creep up his pants leg, but to make sure that Roger Sterling manages to stop before he's gone all haywire. Eleanor, run. Put on your boots and run until you reach the Coney Island rollercoaster, because things are not getting better up in here! Rode the bitch like a horse! In front of you! She was naked and he was fully clothed! It was fucked up! Eleanor pretends that she's this world-weary roué and all this, and Don's like, "You're boring me so bad," and she's like "Don't think of an elephant! And by 'elephant,' I mean 'I am totally slutty!' In case you didn't know!" He tells her it's really not happening, and she's like "Um, pshyeah. Okay, dude." Meanwhile, some stunning dialogue is happening inside that creepy office. Roger's got his head on Mirabelle's thigh and he's kind of absentmindedly running his fingers up and down her leg, and she goes, "I like your office. It's really fancy." He replies that he similarly loves her name, for the same reason I guess, because check it: he wanted to call his daughter Margaret "Margaux," like the wine. And here I thought Mirabelle was as bad as it gets, he throws "Margaux" in your face like it's no big deal.