Don is suffering from toothache but declines Megan's offer to book him a dental appointment. At work, he sees people who look like his dead half-brother, Adam.
At the office, Harry finds out that Joan is looking at more office space on the floor above. Still visibly upset over Lane's suicide, she informs Don that SCDP will receive a $175,000 insurance payout for Lane's death. He tells her to repay Lane's wife the $50,000 Lane gave the company after Lucky Strike left. As she leaves, Don ices his tooth. He later visits Rebecca Pryce and hands her a $50,000 check. After showing Don the photo of Dolores and asking who she is, Rebecca accuses the agency of short-changing Lane and tells him to not leave thinking he has done anything for anyone but himself.
Over at CGC, Ted gives Peggy an unlabelled carton of a Philip Morris' "top secret ladies' cigarette" and tells her to "Smoke it, name it, sell it."
Megan and her friend Emily discuss the difficulty of finding acting work. Emily asks Megan if she will recommend her to Don for a shoe commercial that SCDP is involved with. Megan declines, but later asks Don if he can do this for her. He refuses, asserting that he wants her to be "somebody's discovery, not somebody's wife".
Roger calls the Draper home; when Don answers, he pretends be Emile and asks for Marie. Roger admits to her that he hung up on Megan several times that day and invites Marie to a rendezvous at the Stanhope Hotel. He asks her to take LSD with him, but she refuses.
Pete encounters Howard and Beth on the train; Howard says Beth is going to stay with her sister. Beth later calls Pete at the office, asking him to meet her at the Hotel Pennsylvania. When they meet up, she tells him that she is actually in the city for electro-shock therapy which Howard has arranged to treat her depression. It's not the first time she's done it, and as the side-effects involve memory loss she is upset that she will forget Pete. He urges her to run away with him, but she declines. The following day, he visits Beth at the hospital and finds that she no longer remembers who he is. When he meets Howard on the train, the two get into an argument; Howard, realising that Pete has slept with his wife, knocks him to the ground. Pete then attempts to take his frustrations out on the conductor, who also hits him. When he gets home, Pete claims that his facial injuries are the result of crashing his car. Trudy finally agrees that he should have an apartment in the city.
Joan shows the partners around the prospective new office space. The five partners stand in front of the windows and look out across Manhattan.
Marie chastises Megan for feeling sorry for herself, comparing her to a little girl who wants to be a ballerina. By the time Don comes home, she's drunk and complains that he isn’t giving her acting career a chance. He later visits the dentist for an extraction and, while anesthetized, sees Adam's ghost, who tells him it is not his tooth that is rotten. When Don asks Adam not to leave him, Adam smiles and tells him he will be "hanging around". Afterwards, Don goes to a cinema where he meets Peggy. He tells her that he is proud of her success, but did not know it would be without him. Shortly after this, we see Don looking at Megan's screen test, and he realizes that, while he was talking to Peggy about the whole "success without him," thing, he was talking about Megan. He has in fact been holding her back. He then gets Megan the part in the commercial. On the set, she kisses him and tells him she loves him. He watches her a moment, then walks off. He sits down at a bar and orders an Old Fashioned.
On her first business trip, Peggy sees two dogs mating from her motel room window. She’s shocked, but smiles as she gets into bed with a drink and her work.
Pete is shown sitting in the dark with his headphones on, eyes closed.
Roger is shown standing naked on a chair facing the hotel window, arms outstretched as he has another LSD trip.
A woman approaches Don at the bar, tells him her friend is interested, and asks if he is alone. He turns and looks at her.
This episode contains examples of:
- Ambiguous Ending: Don goes to a bar and is approached by a beautiful woman who asks him, "are you alone?"
- Call-Back: A few:
- Don's guilt for causing Adam to hang himself has been present since he found out about his death in "The Wheel". Lane killing himself in the same way has merely exacerbated this.
- The "top secret" women's cigarette brand that Peggy's working on note is the one Don was chasing prior to writing that letter in "Blowing Smoke".
- Beth arranges to meet Pete at the Hotel Pennsylvania, the same hotel that he waited for her in in "Lady Lazarus".
- Curb-Stomp Battle: Pete's taken down by Howard, and, almost immediately afterwards, by the train conductor he was rude to.
- Electroconvulsive Therapy Is Torture: Averted. Beth willingly undergoes this in order to treat her depression.
- Helpful Hallucination: Don hallucinates seeing Adam several times throughout the episode, who helpfully tells him that it's not his tooth that's rotten.
- I Have This Friend: Pete's excuse for visiting Beth, who by now has no memory of what they did together, is to visit someone else who's in the hospital. This friend is, coincidentally, going through the exact same thing Pete is.
- Ignored Confession: Pete visits a post-ECT Beth and confesses how unhappy he is with his suburban idyll. Via the "I Have This Friend" trope, it goes straight over Beth's head. Invoked in that Pete knows, before he confesses, that the Easy Amnesia has worked.
- It's All My Fault: Joan brings up to Don that if she let Lane fall in love with her, he would still be alive. Don immediately shoots this down.
- Nepotism: Don helps Megan land a commercial with Butler shoes.
- Pun: Adam's ghost (or rather, the vision of Adam that Don sees when he's under anaesthetic) tells Don that he'll be "hanging around".Adam: Get it?
- Rule of Symbolism: Don's rotting tooth is a not-so-subtle symbol of how his life is rotting from the inside. He's also haunted by Adam, a reminder that Lane is not the first person who's hanged himself after Don's turned him away.
- Shout-Out: To James Bond. Don and Peggy see Casino Royale in the cinema, and the episode ends with the theme from You Only Live Twice. Both films were released in 1967, the year in which this episode is set.
- Also, Beth's reading Third Girl by Agatha Christie when Pete visits her in the hospital.
- So Proud of You: Don explicitly tells Peggy that he's proud of her when they run into each other in a cinema.
- What the Hell, Hero?: Rebecca Pryce chews out Don (and the other partners by proxy) for allowing Lane to be consumed by the firm's potential for success.
