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.

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 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 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.

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.

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