Season 5 takes place between Memorial Day 1966 and spring 1967. The season explores Don Draper's new marriage to Megan, which leads him to ignore his work at the Sterling Cooper Draper Pryce advertising agency. Meanwhile, Lane, Pete, Roger, Joan, and Peggy learn that it is "every man for himself" in their personal and professional lives, as they each face painful new beginnings.

Season three takes place six months after the conclusion of the second season and ends in December 1963. It chronicles the end of the "Camelot era" as the characters go through immense change in their professional and personal lives.

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.