It is 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.

Trouble arises on the set of a commercial while Don plays hooky from the office. Meanwhile, Harry, determined to make improvements in his career, tries to gather support around a controversial sponsorship. Betty joins Don when he attempts to appease his clients with a friendly dinner.

Peggy's family hosts lunch for a new priest in their church. Don and Betty enjoy a family weekend together. Freddy and Ken take a client out to lunch who spurs Roger Sterling’s heart. Sterling Cooper staffers work double time to prepare for a last minute pitch meeting.

Don once again finds himself having to deal with issues between TV comedian Jimmy and his wife, Bobbie. Joan finally finds Don the perfect secretary.

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Don buys a brand new car which befits his image as an executive who has "arrived". Elsewhere, Don's secretary makes a grave error, which could spell trouble for Joan, and Cooper has a new piece of art in his office that attracts the interest of the employees at Sterling Cooper.

Freddy Rumsen disappoints his team during a pitch and Pete finds an opportunity at the office to exploit. Meanwhile, Don proves his loyalty to an old friend and Betty finds a welcomed distraction in Sara Beth.

Father Gill convinces Peggy to contribute on a pro-bono church project. Meanwhile, Duck and Don try to create market appeal to a new demographic in order to win the business of an imported beer brand, and Harry is overwhelmed with the workload in his department and recruits assistance from an unlikely source.

Betty visits her ailing father. Meanwhile, Paul's girlfriend Sheila tries to convince him to prioritize his civic duties and Pete's mother disapproves of an idea that Pete and Trudy are considering.

On a business trip to Los Angeles, Don becomes acquainted with some exciting new friends. Elsewhere, Peggy looks for romance at work while Duck starts thinking about the future of Sterling Cooper.

Don meets with an old friend. Meanwhile, an account hangs in the balance when Pete's personal life presents problems and Joan brings her boyfriend to the office.

Sterling Cooper is in play and the office scrambles without Don. Elsewhere, Betty learns some disconcerting news.