Don continues to conceal his increasingly complicated personal life, even in the face of Roger Sterling's invitation to open up. Meanwhile, Peggy pines for the absent Pete still on his honeymoon while fending off the advances of several of the men of Sterling Cooper.

Don and Megan take a trip to Hawaii for the holidays, Sally's friend visits the Francis family, a comedian torpedoes Peggy's Super Bowl ad campaign, and Roger gets some bad news about his mother.

Pete returns from his honeymoon, excited about his new marriage, but conflicted about his past encounter with Peggy. After his business relationship with Rachel takes an unforeseen turn, Don attends a party which further illuminates his increasing dissatisfaction with his present life.

It’s Valentine’s Day, and the Sterling Cooper advertising agency is hustling to stay on top of its game and buzzing over the newest office equipment. Don and Duck find themselves at odds over an account. Betty reconnects with an old friend and once again finds herself struggling with car trouble.

Don strikes up a friendship with the surgeon in his building, Peggy tries to save her campaign, Roger makes a scene at his mother's funeral, and Betty goes to Manhattan to find Sally's friend.

A taboo office romance is revealed. At a brainstorming session, Peggy proves to be more than a secretary, opening up new opportunities for her at Sterling Cooper. Meanwhile, Rachel faces her conflicted feelings for Don after he seeks out her advice on a new campaign.

Trouble arises on the set of a commercial; Harry tries to gather support for a controversial sponsorship; Betty and Don try to appease a client with a friendly dinner.

Don's father-in-law pays a visit to his daughter's family. Peggy works hard on a campaign while the firm tries to decide if they will accommodate an unusual request from a client. Elsewhere, Roger plans a wedding.

As Sterling Cooper Draper Pryce tries to build upon its current business, Peggy is given new responsibility. Don and Harry indulge a client. Betty contemplates her mortality after seeing a doctor.

While Don continues his affair with Sylvia, Pete's latest infidelity threatens his marriage. Meanwhile, Peggy's icy relationship with her new staff continues, but she also gets an unlikely tip on a potential new client.

Roger gives Don some unwanted advice. Peggy and Stan disagree over an account's personnel. Harry asks for Don's blessing.

Pete's professional and personal lives become more complicated as he struggles to assert power in both. While facing pressure from his wife regarding a new apartment, he further alienates Don and endangers his own position at Sterling Cooper.

Paul hosts a party at his apartment and introduces someone special to his Sterling Cooper colleagues. Peggy visits her family for dinner. Despite a conflict of interest, the Sterling Cooper agency aggressively pursues an airline account and Duck attempts to appeal to the client using an unorthodox approach.

Don and Duck try to make peace; Peggy tries to get into the executive's after-hours meetings; Duck deals with a family visit.

Betty visits her father; Paul's girlfriend tries to convince him to prioritize his duties; Pete's mother disapproves of his and Trudy's idea.

Don decides to include Betty on a company business trip. Pete lends a hand to a neighbor in his apartment building.

Things quickly become awkward after the two firms merge, Don asserts his dominance over Sylvia, Pete has to deal with his ailing mother, and Bob Benson helps out a sick Joan.

Don makes a new friend. Joan meets a client for drinks. Peggy hears impressive new work. Roger has a puzzling phone call.

Don and his father-in-law cross paths. Meanwhile, Peggy is in search of a new roommate; and a rich new client is excited to be doing business with the firm.

Sally's behavior causes concern for Don and Betty. Betty has an eye-opening dream that has a strange effect on her. Pete tries to work a new business angle in his dealings.

Don attempts to regain his creative spark, but undermines a member of his staff while doing so. Roger pursues some new clients, and in the process, hurts Jane. Betty displays her pettiness when she reveals a distressing secret to Sally.

Don works in secret on a Heinz ketchup campaign while Megan gets a love scene on the set of her soap opera. Meanwhile, Harry makes his power play while Joan has more trouble with the secretaries.

In 1960 New York City - the high-powered and glamorous "Golden Age" of advertising - Don Draper, the biggest ad man in the business, struggles to stay a step ahead of the rapidly changing times and the young executives nipping at his heels.

After Don wins an award, his photo is featured in Advertising Age. Don must deal with the fallout as the photo brings back a past he isnt ready to confront. Ken gets a short story published in The Atlantic Monthly, inciting jealousy among his colleagues and driving Pete to make an unorthodox request of his wife. Peggy overhears a startling conversation in the office and shares the secret with Joan.

Roger joins Don for an evening of dinner and drinking, during which Roger's behavior leads to a rift in their friendship. Though Don accepts his apology, there are further consequences for Roger. Pete faces trouble at home as he continues to struggle with the demands of his new marriage.