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.

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.

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.