Don is tormented as pieces of his secretive past begin to haunt him. Peggy's new success at work, and resulting boost in confidence, threaten her office relationship. Salvatore Romano gets a little too close with a client.

A rival ad agency courts Don, involving Betty in their attempt to lure him from Sterling Cooper. As the presidential campaign heats up, the agency looks for new ways to counter the latest Kennedy ads. Tempers flare over Peggy.

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.

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

Don and his father-in-law cross paths. Meanwhile, Peggy is in search of a new roommate; and a rich new client is excited to be doing business with the firm.

Sterling Cooper receives a surprise visitor; Sally has been spooked by something (or someone); and Joan receives some shocking news.

The firm celebrates as they hit a milestone. Peggy and Paul compete to secure the same account.