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

The writers make an attempt to stave off late-night boredom during a mandatory overtime session. Roger throws a party as Joan and Greg host their own party. Sally has a run-in with Grandpa.

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

There is trouble for Don and Sal in giving their clients what they ask for. Meanwhile, Betty hosts a fundraiser.

A former client makes a return; Betty and her kids go on a trip; and Joan and Greg make plans for their future.

Don has a big meeting with Connie about their future relationship. Betty is the beneficiary of some interesting advice and Pete has a serious sit-down with some clients.

Don and Pete disregard Roger's plans in order to land a new client.