Jessica Paré

A carousing college professor's life takes a series of unimaginable turns, and all the old stories are given a new twist, when he begins to have surreal hallucinations.

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 6 takes place between December 1967 and November 1968. It begins with Don and Megan taking a trip to Hawaii for the holidays. Sally's friend visits the Francis family, a comedian torpedoes Peggy's Super Bowl ad campaign, and Roger gets some bad news about his mother.

Season 7 begins in January 1969, several weeks after the Thanksgiving 1968 ending of season 6, and ends in July 1969, with characters dealing with the dynamics of lives and offices being split between New York and Los Angeles.

Matthew, a young advertising executive in Chicago, puts his life and a business trip to China on hold when he thinks he sees Lisa, the love of his life who left him without a word two years earlier, walking out of a restaurant one day.