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.

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.

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.

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.

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.

Don is tormented as pieces of his secretive past begin to haunt him. Peggy's new success at work, and resulting boost in confidence, threaten her office relationship. Salvatore Romano gets a little too close with a client.

In the midst of a crisis, Don runs into an old friend.