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.

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.

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.

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