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.

Don attempts to track down a friend, Joan tries to solve a problem with an account and an unlikely person sets up Peggy.

Don comes up with a big idea, Roger asks Joan to help him fix a clerical error and Peggy has difficulties casting for a commercial.

Don receives a reward for his work. Joan butts heads with her co-worker on an account. Faced with a big decision, Roger dodges.