Don's bag has never been being himself, but also not staying faithful. When he returns from vacation, his writing staff (including a new female writer, who looks like some sort of frumpy combo of Peggy and Jan) are working on a campaign for an oven cleaner.
The company wants them to use the word "love" and their first ad mock-ups include a imagery of an affectionate married couple in their kitchen.
"Anything matrimonial feels paleolithic," Don tells him. Yikes, 1967 is rough. And 1967 also means the writing staff, especially fully bearded Stan is both sporting some wild facial hair and smoking weed in the office. Was this a thing that really happened? The reefer part, not the facial hair part.
Don spends much of this episode in a fog. It's easy to see just how unhappy he is with his great-on-the-outside life, and how focused on his own mortality he is (I'm guessing Lane Pryce's death is very much still fresh on his mind). During a darkly funny memorial service for Roger's dead mom (more on this later), a drunk/out of it Don throws up.
Don's downward spiral to sadness and self-hatred is exposed in the most unlikely of places: an ad pitch. This is where Don usually shines and keeps the private stuff private. But his proposed ad for the Royal Hawaiian is depressing: It looks like a man walks off a plane, gets undressed and kills himself by drowning in the ocean. He even calls the ad "Hawaii: The jumping off point" and goes on and on about how different cultures believe the soul can go in and out of the body.
What happened to the man in the ad, the confused clients ask. He shed his skin, Don says.
"We sold actual death for 25 years with Lucky Strike," Roger tells Don. "You know how we did it? We ignored it."
Yeah, not your best work, Don.
One of the final parts of the episode is a boring New Year's Eve party at Don and Megan's with some of their friends in the building (there's fondue! And a Hawaiian vacation slide show!). While we saw building friend Dr. Rosen earlier in the episode, we meet his wife, Sylvia (played by random guest star Linda Cardellini) and a few other annoying people, including one flirtatious middle-age blonde whom you are lead to believe is sleeping with Don.
But, no. Weiner is full of surprises when he's not handing down obvious metaphors. After we have to endure Don talking about death some more, this time with Dr. Rosen ("What's it like to have someone else's life in your hands"? he asks the doc), Don enters the Rosen apartment and sleeps with Sylvia.
"Did you read my Dante?" she asks.
"It made me think of you," he says.
And there's this ambigious episode end: "I want to stop doing this," Don says.
"I know," Sylvia responds.
Does he mean the affair? Does he mean lying to Megan and Dr. Rosen? Does he mean having to sit through Weiner's labored symbolism? So many questions.
Roger Sterling: Roger is by far the stand-out of this episode (welcome back, John Slattery!), from his hilarious therapy session (I would pay Roger to sit in on his sessions) A credit to Slattery: He's in full mid-life crisis mode, but his acting never seems forced and cliched.
Roger is back to his good old sardonic self, especially when his secretary, Caroline, tells him that his 91-year-old mother passed away. He tells her that it's not really a surprise -- she was old as hell -- but he doesn't shed and tear and looks blankly at his secretary when she hilariously says, "She was always so polite to me. When she could hear me."
But Roger at his mother's funeral/memorial service? Pure gold. Maybe equal with his LSD trip (really). We not only get to see him interact with two ex wives (yep, Jane and Mona received invited), but watch his Emmy-worth eye-rolls as one of his mom's friends gives the worst eulogy ever (Don even throws up after the woman says that Roger' mom used to say, "My son is my sunshine"). This part played out like a huge black comedy. After yelling at Mona's new man, Roger fnally yells "THIS IS MY FUNERAL" (yep, Weiner-ish heavy-handedness) before he softly confides to Mona that he regrets not spending enough time with his mom.
"I looked out at that crowd and just saw a bunch of women I disappointed," he admits.. Have we ever seen Roger be so vulnerable? I doubt it.
Betty Draper: I was surprised to see January Jones get as much screen time as she did in the premiere, especially after her very limited appearances in Season 5.