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.

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.

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.

A rival ad agency courts Don, involving Betty in their attempt to lure him from Sterling Cooper. As the presidential campaign heats up, the agency looks for new ways to counter the latest Kennedy ads. Tempers flare over Peggy.

Peggy is given a difficult assignment. Roger's work problems provide new opportunities for Don, and Pete grows more frustrated. Betty finds a new outlet for her growing dissatisfaction.

As Thanksgiving approaches, Don's work responsibilities interfere with his domestic life. Peggy is given a new opportunity, provoking the ire of some of her colleagues. Betty makes a startling discovery.

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.

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.

The office scrambles without Don; Betty learns some disconcerting news.

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.

Betty tries her hand at local politics. Don is forced into thinking about the future. Peggy receives a luxurious gift.

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

There is trouble for Don and Sal in giving their clients what they ask for. Meanwhile, Betty hosts a fundraiser.

Joan and Peggy deal with high-jinx in the office.