Don and Megan take a vacation to Hawaii for a new client, Sheraton Hotels. Megan is repeatedly recognized as an actress on a popular Soap Opera, To Have And To Hold. Meanwhile, Don meets a young soldier, PFC Dinkins, in a bar. Dinkins is getting married the following day and persuades Don to give away the bride (her parents being unable to make it). Upon returning, they consult with Jonesy, the building's doorman, who had a heart attack before they left but was saved by the intervention of another resident, Dr. Arnold Rosen. Don and Arnold have struck up a friendship.
Back in New York, Roger receives news of his mother's death. At the wake, his estranged daughter Margaret attempts to cajole him into investing in her husband's refrigeration business idea, although the whole thing is cut short when a drunk Don throws up and Roger becomes annoyed that Mona has brought her new husband. Peggy is thriving at her new job at CGC. The company encounters a crisis when a comic on The Tonight Show makes a joke about American soldiers cutting off the ears of defeated Viet Cong as war trophies, making CGC's next planned work — a campaign about headphones revolving around the slogan "Lend Me Your Ears," which will air during the Super Bowl — rather poor in taste. Peggy's quick thinking defuses the crisis and finds them an out. Ken Cosgrove becomes suspicious of the intentions of Bob Benson, an new and very eager-to-please junior accounts man. Betty engages in some parenting of Sally's friend Sandy, a violin prodigy who is going to Juilliard; later she goes to Greenwich Village to try to rescue Sandy, and decides to change her look after a confrontation with Village squatters. Finally, Don is revealed to be having an affair with his neighbor, Sylvia Rosen.
This episode contains examples of
- Amicable Exes: Roger and Jane are on much better terms by this episode. She offers to return his mother's wedding ring during her wake, but he insists that she keep it.
- Bratty Teenage Daughter: Sally displays snarkier behavior towards Betty this episode.
- Call-Back:
- This episode has the Drapers showing off their Hawaiian vacation pictures with a Kodak Carousel, a Call-Back to Season 1 finale "The Wheel".
- The Reveal of Don's new girlfriend at the end of that episode is highly reminiscent of the reveal at the end of the pilot that he's married with a family.
- Before their meeting about the "Lend me your ears" slogan, Peggy asks Burt Peterson how his Christmas went. In response, he reminds Peggy that he is a widower. This calls back to season 3, episode 1, when his wife was said to have cancer when Burt was fired from Sterling Cooper.
Burt: How was your Christmas?Peggy: Same as the last five, ruined by work. How was yours?Burt: I'm a widower, Peggy.Peggy: Oh. I'm sorry. - Christmas Episode: The episode takes place at the dead-end of December 1967.
- Defcon 5: Discussed Trope, as Peggy has to explain to her boss what the DEFCON levels actually mean.
- "Eureka!" Moment: Peggy breaks the Koss headphones campaign after she watches Abe using the headphones and being enraptured by the music. She comes up with an ad using outtakes of the actor, with the tagline "Koss headphones: sound so sharp and clear you can actually see it."
- Everyone Has Standards: Pete, of all people, sounds visibly disgusted when Harry expresses his arousal towards Margaret.
- Ms. Fanservice: During Megan's stay in Hawaii, she's gotten into the habit of sleeping nude, with a scene showing her getting out of bed, shrugging off the Modesty Bedsheet and doing a morning stretch, with her bare back to the camera.
- Freudian Couch: As per tradition, Roger lies on a couch facing away from his therapist.
- The "Fun" in "Funeral": Roger's mother's wake has food getting sent over by Bob Benson in an attempt to impress Roger, Harry perving over Margaret, and Don getting so drunk that he vomits during a touching speech given by one of Roger's mother's friends (forcing Pete, Harry, and Ken to get him out). It ends when Roger kicks everybody out after realising that the strange man Mona has brought with her is her new husband.
- Manly Tears: Roger at the end of the episode, when he receives the shoeshine kit from the shoeshine guy who has died (he asked that it be given to Roger because he was the only one who asked him how he was), but is obviously also crying about his mother's death earlier in the episode.
- Multi-Part Episode: Much like the previous season premiere, this episode is actually two counted as one.
- New Year Has Come: The episode ends with Dec. 31-Jan. 1, 1967-68. Don and Megan have some neighbors over for a New Year's party.
- Nice to the Waiter: Roger was this to the shoeshine guy, which is why he ends up with his shoeshine kit.
- Professional Butt-Kisser: Bob Benson has shades of this, when he gives Don a cup of coffee and when he has some catered food delivered to Roger's mother's wake.
- Racial Face Blindness: Dinkins, who's on leave from Vietnam, expresses this belief to Don, saying they "look just like the enemy".
- Shout-Out: Quite a few.
- On the beach, Don's reading a copy of Dante's Inferno.
- Peggy's "lend me your ears" tag-line for the headphone advert is a quote from Shakespeare's Julius Caesar (which is why the actor in the ad is wearing a toga). It has to be dropped after a joke on The Tonight Show about war crimes in Vietnam (specifically, about US soldiers cutting the ears off dead VCs), although Peggy is able to save the day by using out-takes which only show close-ups of the actor's face and coming up with a new tag-line.
- To Have and to Hold, the soap Megan now stars in, is set in a town called Berkshire Falls — not a million miles from Bedford Falls, perhaps?
- Roger asks Don if he was chased by Ernest Borgnine with a knife while in Hawaii — a nod to From Here to Eternity.
- The ad that Don pitches for Sheraton is unfortunately very reminiscent of the ending of A Star is Born where a character commits Suicide by Sea. This is pointed out in universe.
- Vomit Indiscretion Shot: Don at Roger's mother's funeral, after getting an early start on his drinking. It just so happens that he does this during a rather cloying eulogy by one of Roger's mother's friends. Roger, of course, has the last word on the subject.Roger: He was just saying what everyone was thinking.
- What the Hell, Hero?: Betty tries to initiate foreplay by suggesting that Henry rape Sally's friend who is staying over. He's appalled, and calls her out on it.
