- Don flies to Los Angeles to visit Anna before his New Year's vacation to Acapulco, but her bad news influences him to cancel his vacation and return to New York, where he discovers that Lane has problems of his own.
- Plans are being made for the New Year's break. Don, heading to Acapulco, makes a twenty-four hour stop in Los Angeles to visit with Anna, who's broken her leg which is in a cast. The two spend the day with Anna's grown niece, Stephanie. Alone with Stephanie at the end of the evening, Don tries to seduce her, but his seduction plans change when she gives him some sobering news. Don has to figure out what to do with the news before he leaves Los Angeles. Because of the news, Don changes his New Year's plans. Back in New York, Joan and Greg want to start a family, but have to find time when both are free. Lane denies her the two days she wants in January when Greg is off, after which she expects he will be headed to Vietnam at the completion of basic training. Lane's attempt to make it up to Joan which goes slightly awry and a mishap at home combined with the underlying stress of trying to find the time with Greg finally take their toll emotionally on Joan. And Lane was supposed to go back to England to spend time with his family, but for personal reasons decides to stay in New York to work instead, work which is his new grounding in life. He gets some unexpected company, the two who paint the town for January 1st, 1965, which provides Lane with some much needed distraction.—Huggo
- As the New Year approaches, several of the staff are planning holidays. Dick is planning a holiday in Acapulco but spends a day en route in Los Angeles with Anna Draper. Don learns some shocking news about Anna from her niece. Joan has a check-up with her doctor as she and Greg are thinking of starting a family. Her request for a few days off later in January to accompany Greg to Texas for his basic training is gruffly rejected by Lane Pryce. His attempt at an apology leads to even harsher words and a firing. On a drunken night out, Lane reveals a different side of himself.—garykmcd
- Joan Holloway is in the examining room, her doctor Walter has just finished and lets her know she should be able to have kids even after two "procedures". He assures her there should be no problems, but is puzzled by the timing, since her husband Greg (Samuel Page) will soon be shipped off to Vietnam
Don Draper comes into the office for a half day work before leaving for a trip out West. Harry comes in to talk shop, then Lane arrives with a folder of papers for signature. He wishes Don Happy New Year. The secretary comes in and Don asks her about her New Year's plans.
Joan goes to see Lane to ask for some time off in mid-January, he refuses.
Don has a day stopover in Los Angeles and goes to visit Anna Draper (Melinda Page Hamilton). They greet each other warmly, Anna broke her leg recently. Anna's sister Patty (Susan Leslie) comes over to help with the chores, with her daughter Stephanie (Caity Lotz), who is at Berkely. Stephanie stays behind when Patty leaves, and the three go out for dinner at a roadhouse.
Joan arrives back at the apartment as Greg is leaving for night shift. They argue about her not getting time off in January, and he leaves for work abruptly.
Stephanie talks about college life and questions Don about his, he says a few non-consecutive years in night school at City College. Don offers to bring the kids out in the spring, Anna is excited. They talk about Don's marriage and how Betty "broke your heart" (!). Stephanie and Don slow dance to the jukebox. Later, Don drives Stephanie home, they chat, Don makes a pass at her in the driveway. She turns him down and instead tells him that Anna has cancer, and does not know herself. In the morning Don starts painting Anna's living room, when Patty arrives Don angrily confronts her outside about the secrecy, and says that he will pay for any possible treatment. Patty replies that they have already consulted experts, who all agree that the cancer is terminal. She asks him to stay out of the family's business. Don reluctantly decides to acquiesce. Sharing a joint of marijuana, he tells Anna he has to leave, going back to New York instead of Acapulco but will return at Easter with the kids. He signs the base of the wall "Dick + Anna 1964".
Back at the office Peggy delivers a box of red roses to Joan. Joan reads the card, "Darling, I've been an ass. Kisses, Lane." and is furious, storming off to Lane's office. He assures her that the note was intended for his wife, and that the mistake was made by his secretary, Sandy. Lane and Joan ream out the befuddled woman and Joan fires her.
At their apartment, Joan greets Greg with a Hawaii themed dinner prepared but he has eaten already. Perturbed, she goes to cut some oranges but slices her hand. Greg pulls out his black bag and stitches her up, Joan is won over by his bedside manners.
Back in New York on 31 Dec, Don meets Lane in the office, Lane offers a drink of an expensive liquor, a gift from his father, Lane tells Don they've had a "magnificent year". Awhile later Don calls him and takes Lane out for steak dinner, where the Brit admits his wife is not coming back to New York. Later the two go to a Godzilla movie, standup comedy (where the comic pokes fun at the two men) and finally, hookers. Back at Don's apartment, Lane spends the night with one of the girls. In the morning Lane asks Don how much for the girl, Don replies $25, Lane gives him 30, thanks Don for the "welcome distraction", and leaves. Don flops on a bed to sleep.
Back at the office, the Joan, Don, Roger, Lane, Harry and Pete convene for a meeting. Joan opens with the words "Gentlemen, shall we begin 1965?"
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