Porpoise Song
performed by The Monkees

The Monkees are tossed about in a psychedelic, surrealist, plotless, circular bit of fun fluff.

Roger tells Don of a potential new client, Sunkist. They inform Ted prior to their partners meeting and Ted loses his temper because he and Jim have been preparing a proposal to land Ocean Spray, which would present a conflict. Sally and her friend, Julie, are staying with Don and Megan in order to attend a Model U.N. meeting in Midtown. In the lobby they meet the Rosens' son, Mitchell. Megan learns that Mitchell has dropped out of college and has been classified as 1-A, making him eligible for the military draft. Don then discusses Mitchell's situation at a client dinner that evening with Chevy, and the next morning Ted informs Don of a connection he has in the Air National Guard that can help with Mitchell's situation, but only agrees to help if Don drops Sunkist. Don tries to contact Dr. Rosen and gets Sylvia instead, who is overjoyed that Don has intervened. Julie informs Sally that she wrote a love letter to Mitchell, signed Sally's name, then slipped it under door of the Rosen's apartment. Sally goes back to the building and receives keys for the hotel from the doorman. Sally goes to to the Rosen's apartment to retrieve the letter and sees Don and Sylvia having sex, and Sally runs out of the room. Later that night Don returns to his apartment, and Dr. Rosen and Mitchell drop in to thank Don. Sally storms off to her room. Sally locks the door and Don tries to explain that Sylvia was upset and he was only trying to comfort her, adding that the situation is "complicated." Don asks Sally if she understands and goes off to bed

While on a hunting trip in Michigan with two Chevy executives, Ken Cosgrove is accidentally shot in the side of his face with buckshot. Back in New York, Ken confides to Pete Campbell that he can no longer deal with the personal stress that Chevy is causing him. Pete sees this as his opportunity to finally handle Chevy and suggests to Ken that he manage the account. The firm's partners agree to the arrangement, and have Bob Benson on the account, too. Pete learns from Duck Phillips that Bob lied about his background. Pete tells Bob of his discovery, but reveals nothing to the firm so that he can maintain control over Bob. Don takes a day off from work, and Harry Crane calls to tell Don that Sunkist wants to expand their print ad campaign to television. Don cites the conflict with Ocean Spray, but Harry insists to the point where Roger and Don inform Jim and Ted about the development. Don tries to make it up to Ted by backing him up during a pitch to St. Joseph Aspirin, but warns Ted that his affection toward Peggy has been clouding his judgement. Betty informs Don that she and Henry are considering sending Sally to boarding school for girls. Betty and Sally take an overnight trip to visit a school. The next day, while driving home, Betty informs Sally that the school's feedback about her was positive.