First, the bad news.
Lane is having marital problems, as well as his share of disagreements with Joan, so he sends roses to his wife ("Darling, I've been an ass"') and to the aforementioned office manager ("Joan, forgive me"). Except that his secretary switched them around, so his marriage is over.
Don plans to spend New Years' in Acapulco. With a 24-hour layover in Los Angeles, he visits Anna, her sister Patty Horton and her niece Stephanie (studying at Berkeley!). Anna has a broken leg, and Stephanie reveals to Don that her bones are frail because she's dying of cancer. This news causes Don to stay in Los Angeles a little longer, paint over a stain on the wall from a leaky roof, sign the new paint job with "Dick + Anna '64," and sit around smoking pot and talking about UFOs. He won't tell her she's dying, but he promises to bring the kids come Spring Break. He gives up on Mexico and returns to the office.
Now, the good news.
It's officially 1965. Don and Lane find each other at the office and drown their sorrows in strange liquor, hilariously going to the theater to heckle Gamera, lame stand-up comedy, and call girls. Although it's been precarious financially, it's been a magnificent year.
This episode contains examples of:
- The Corrupter: Don, in his grief learning of Anna's cancer, plays this role for Lane, including getting him to cheat on his estranged wife with a prostitute.
- Deliberate Values Dissonance: It was considered ethical back in the 1960s for a doctor to withhold a terminal cancer diagnosis from a patient[1]
. However, Don is still horrified by the idea. - The Ditz: Lane's secretary Sandy is this.
- Fanservice: Lampshaded by Anna when she says, "I'm not going to fight Dick Whitman painting my living room in his shorts."
- Jerkass Has a Point: Joan's doctor is weirdly inappropriate and intrusive into Joan's business (the last time we saw him was when he threatened Peggy with taking away her Pill if she sleeps around) but he does share apprehension about what sort of man Joan is married to.
- Mistaken for Gay: The stand-up comic who Don and Lane go to watch attend does a routine about them being a couple. It's a joke, but Lane is quick - too quick? - to correct him.Comic: [noticing Don and Lane's dates arriving] I guess I was wrong. You're not queers. You're rich.
- Mood Whiplash: The episode zig zags between funny and dramatic, complete with Joan's bloody hand.
- Never My Fault: Sandy, Lane's (former) secretary, who places the blame for the mix up of mailed roses to both Rebecca Crane in London and Joan on the florists and not her own incompetence. Joan calls her out on it.
- One Crazy Night: The final act of the episode features Don and Lane celebrating New Year's Eve in Manhattan. Bored and lonely at the office, they decide to see a Japanese Kaiju film, order a nice steak dinner, see an open mic act, and enjoy the company of call girls - all while drinking throughout.
- Pet the Dog: Greg has a surprisingly heartwarming moment with Joan when he gets to show off his doctor skills and sew up a cut on her hand. It turns out that, despite his lack of surgery skills, he has a really great bedside manner.
- "The Reason You Suck" Speech: Joan delivers this to Sandy, Lane's soon-to-be-former secretary.Joan: Sandra, everyone makes mistakes. But the fact that you’re the kind of person who cannot accept blame is egregious.Sandra: I don't know what that means.Joan: It means I can’t believe I hired you. You're fired.
- Shout-Out: Among the movies Don and Layne discuss seeing are The Guns Of August, It's a Mad, Mad, Mad, Mad World, Send Me No Flowers, The Umbrellas of Cherbourg, and Zorba the Greek. They end up seeing Giant Monster Gamera instead.
- Waxing Lyrical: Joan's doctor tells her, "Whatever will be, will be," which is from "Que Sera, Sera".
- What the Hell, Hero?: Patty and Don give one of these to each other; she because she thinks Don slept with Anna and Stephanie, he because he's angry about the fact Patty has kept the news about Anna's terminal cancer from her.
