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.

Don loses an account. Roger, stuck in the city for Labor Day weekend, attempts to cheer him up. Meanwhile, Joan has a night out on the town with her roommate.

Peggy's family hosts a lunch for their church's new priest; Don and Betty enjoy a weekend together; Pete and Ken take a client out to lunch; the staff works to prepare for a last minute pitch meeting.

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.

Peggy's taste in men proves questionable. Pete has to make a big decision about his career and a candidate makes a big impression on Don.

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.

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.

Peggy becomes unsatisfied with her apartment and with Abe, Don has an eventful weekend with Betty while Megan has problems on the set, Roger has time with his grandson, and Pete begins exploring his options outside the firm.

With his personal and professional life crumbling around him, Don positions himself for a change of scenery. Meanwhile, Pete's life is falling apart as well, thanks to the meddling of Bob Benson.

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

Sterling Cooper & Partners prepares for a guest; Don contacts an old friend; Roger deals with problems at home; Peggy is underestimated.