At an advertising agency in 1960s Manhattan, the creative director has problems coming up with ideas for a tobacco account and crosses swords with the female head of a large department store that she wants to take in a new retail direction.
Betty sees a specialist about her ongoing physical problems; a managing partner leans on Don to get involved in the Richard Nixon presidential campaign; Peggy gets some unwanted attention from a copy writer.
Pete's return from his honeymoon stirs up conflicted emotions about his bachelor-party dalliance with Peggy; Don and Rachel's business relationship shifts; Betty sets tongues wagging when she invites the neighborhood divorcée to her daughter's birthday party.
Pete oversteps his bounds in dealing with a valuable client, puts his foot in his mouth and gets a lesson from Don in toeing the company line. At home, he gets pressure from his newlywed bride to buy their own apartment unit.
Don wins a prestigious award and gets his face splashed on a prominent industry periodical, which triggers some fallout from his past; Ken gets a short story published in a national monthly magazine, inspiring jealousy among his colleagues.
Peggy offers superb suggestions during a focus-group session, and her ideas are so well received that her future at the agency looks much brighter; Don asks Rachel's advice about an ad campaign for Israeli tourism.
A boys' night out for Roger and Don ends badly as Roger's erratic behavior damages their relationship; Pete encounters problems on the home front as he and his bride continue to adjust to being married.
Don's mysterious past comes back to haunt him; Peggy celebrates her new work success, but not all of her colleagues and co-workers are pleased or impressed; Salvatore's relationship with a client is questioned.
A rival ad agency tries to poach Don from Sterling Cooper, and they involve Betty in their campaign to land him; romantic rivals vie for Peggy's affections. Also, the agency steps up its Nixon presidential campaign in an attempt to counter successful Kennedy promos.
Don is distraught about losing an important account, so Roger, stuck in the city on Labor Day, tries to cheer him up; Joan and her roommate paint the town.
Peggy is assigned a difficult project; Don seizes the opportunity provided by Roger's latest work woes; a frustrated Pete develops more problems at home and in the office; Betty seeks new relief for her mounting frustrations.
The Sterling Cooper staff pulls an all-nighter watching Nixon-Kennedy election returns; an ambitious Pete directly challenges Don.
Peggy's colleagues are irked when she's given a new job opportunity; Don's work responsibilities get in the way of his home life; Betty uncovers a surprising secret.
