Season two takes place between February and October 1962, culminating with the Cuban Missile Crisis. It expands on Peggy's rise in the workplace and the marital strife between Don and Betty Draper as Don's infidelities further intrude on his family life. The second season also introduces an unknown acquaintance of Don Draper. Draper is corresponding by letter with this unseen acquaintance in secret.

Season one takes place between March and November 1960. It introduces the fictional advertising agency Sterling Cooper. The season begins with the new secretary, Peggy Olson, starting her first day with the firm. As the season unfolds, the mysterious backstory of enigmatic ad man Don Draper is revealed as are the growing confidence and success of Peggy Olson.