Set in 1960 New York City, in an unexpected new world - the high-powered and glamorous "Golden Age" of advertising - where everyone is selling something and nothing is ever what you expect it to be. The drama unfolds around Don Draper (Jon Hamm), the biggest ad man in the business. As he calls the shots in the boardroom and the bedroom, he struggles to stay a step ahead of the rapidly changing times and the young executives nipping at his heels.
Over the din of the Xerox machine, Peggy brainstorms with Ken and Sal about the Popsicle campaign. Sal and Peggy recall their mothers' ritual of breaking popsicles in half for the kids to share. Pete, meanwhile, learns that Trudy has scheduled an appointment with an adoption agency.
Bertram's sister Alice visits him to discuss the proposed sale of Sterling Cooper. She finds the terms generous, but Bertram fears the merger will leave him feeling "as useful as the Queen of England."
Don, still in Southern California, flashes back to a long-ago meeting with the wife of the real Don Draper. Asserting that he's "been caught," she begs him to reveal her husband's fate. After initially resisting, Don tells the woman, Anna, that her husband died in combat.
Back in the present, Don visits Anna in California. One of her piano students is playing "In the Hall of the Mountain King." "It's scary," Don tells the boy. "Are you in trouble," Anna asks Don after the boy departs.
"We are not adopting a child. That's final," Pete declares to Trudy. The same night, Greg loses interest during lovemaking when Joan gets on top of him after saying, "You're tired, let me do the driving." Moments later he apologizes for not knowing "all the things" she wants in bed.
Sipping beer on Anna's front porch, which, she reminds him, he paid for, Don says, "I've ruined everything. My family, my wife, my kids." He describes himself as merely "watching" his life. "I keep scratching at it, trying to get into it. I can't."
Pete receives a call from Tom Vogel, his father-in-law, who is putting the Clearasil account up for review, despite what Pete calls spectacular results. Pete is "distracted," Tom contends, because Trudy is unhappy; it's affecting his work. Tom should just pull the account right now, counters Pete, and stop meddling in his and Trudy's marriage.
Don flashes back to a Christmas Eve with Anna. Betty, the new woman in his life, is "so beautiful" and happy, he says. Don wants to marry her, but he and Anna will have to divorce. Anna consents; having a family will give Don "a chance at a whole new life."
Peggy presents the Popsicle campaign: "Take it. Break it. Share it. Love it." Her approach impresses the company's representatives.
Betty calls Sarah Beth, who admits to making "a terrible mistake" with Arthur Case, their friend from the stables. When Betty chides her for not knowing the difference between "wanting and having," she accuses Betty of encouraging her to have an affair. "No one made you sleep with him," Betty retorts.
After a repairman lectures Peggy about her coworkers' abuse of the copy machine, she tells Roger she brought in the Popsicle account on her own and requests Freddy Rumsen's old office. "It's yours," says Roger. "You young women are very aggressive," he notes approvingly.
In Don's office the same afternoon, Greg asks Joan to "pretend I'm your boss" and forces himself upon her despite her protest that "this isn't fun." He pins her to the floor, saying, "This is what you want, right?"
The next day, Bertram, Alice, and Roger meet to vote on the merger. Don's small share of the company makes his absence irrelevant, says Bertram. The partners agree to sell.
Joan congratulates Peggy on her new office. Peggy returns the compliment, calling Greg "a keeper." Ken and Harry stop by with Paul, who has returned from Mississippi. He describes his trip as the adventure of a lifetime. "I'm the head of Television," Harry complains when he realizes that Peggy has gotten Freddy's office.
Betty gives Sally some new riding boots. She tells Sally that she and Don have had a "disagreement" and that she doesn't know where he is or when he'll return. In California, Don repairs a chair while Anna does a tarot reading. The chair fixed, he notices a copy of Frank O'Hara's Meditations in an Emergency. She says the poems made her worry about him. Asked if he should be worried about the cards, she says they reveal that he's unhappy only because he believes he's alone.
"I'm sleeping with Don," Peggy jokes when Pete asks how she scored her office. Pete chuckles before informing her that Clearasil is pulling its account. When Peggy asks what happened to Don in California, Pete says Don just disappeared. Hinting that he knows things about Don's past, Pete adds, "He may not be coming back. He's done it before."
Back in California, a shirtless Don walks into the ocean, his eyes closed as the waves crash against him.