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.

Trouble arises on the set of a commercial; Harry tries to gather support for a controversial sponsorship; Betty and Don try to appease a client with a friendly dinner.

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.

Don has to deal with issues between a TV comedian and his wife; Joan finds Don the perfect secretary.

Don and Duck try to make peace; Peggy tries to get into the executive's after-hours meetings; Duck deals with a family visit.

Don buys a new car; Pete, Harry and Ken strategize to attract new business; Don's secretary makes a grave error; Cooper has a new piece of art in his office.

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

Betty visits her father; Paul's girlfriend tries to convince him to prioritize his duties; Pete's mother disapproves of his and Trudy's idea.

Don makes some new friends on his trip to Los Angeles; Peggy looks for romance; Duck ponders the future of Sterling Cooper.

Don meets up with an old friend; Pete's personal life presents problems; Joan brings her boyfriend to the office.

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