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Summary SCREENRANT VIDEO OF THE DAY SCROLL TO CONTINUE WITH CONTENT Don Draper had 19 mistresses throughout Mad Men's seven seasons, not counting his three wives, making all of Don Draper's mistresses difficult to keep up with. Mad Men was one of AMC's prestige series that followed the lives and careers of Madison Avenue advertising executives throughout the 1960s. While the other ad men of Sterling Cooper also carried on extra-marital affairs, Donald F. Draper had the most by far.
Midge is also a swerve as audiences are initially led to believe she is Don's significant other before the end of the first episode reveals Don has a wife, Betty, and two young children in the suburbs.Don's fling with Midge ends in season 1 when he discovers that she is in love with one of her male friends and she refuses to go on a trip with him. She reappears in Mad Men season 4 where she is married to someone else.
Don abandons Pete Campbell and stays with Joy and her strange, aristocratic friends for a few days before he leaves to visit Anna Draper and then return to New York. Of all the Don Draper mistresses, the free-spirited Joy may have been the youngest of them all. Perhaps Bobbie's biggest contribution to the series is her advice to Peggy that she cannot win by trying to be a man in the business world but can use being a woman to her advantage. Don ends their Mad Men season 2 relationship when he learns Bobbie has been gossiping about his prowess in the bedroom.
However, the real fallout of Don's Baltimore trip was his discovery that Sal is a closeted homosexual, which later led to Romano's dismissal from Sterling Cooper. In that sense, Don is shown to be a massive hypocrite, having an affair with Shelly while on the trip but getting angry at Sal for doing the same thing simply because it was with another man.
Later in season 4, Draper introduces Lane Pryce to Candace and her friend to cheer him up when his marriage is on the rocks. They go back to Don's apartment but Lane notices that Candace seems to have a familiarity with the apartment, realizing that she and Don have some previous connection with each other.
Related Mad Men: Why Lane Pryce Killed Himself Lane Pryce's death in Mad Men was a shocking tragedy but Lane taking his own life was actually teased with a sly joke in the season 5 premiere. 9 Alice & Doris Played By Amy Motta & Becky Wahlstrom Close The combination of two very brief affairs with two different women are used to show the further spiraling nature of Don's behavior. When Don wins a Clio Award in Mad Men season 4's "Waldorf Stories," he goes on a bender that lasts for days. Don goes to bed with Alice , a woman he picks up at a bar while he's celebrating his Clio.
However, when they start to develop more of a professional relationship, Don becomes interested in moving it into unprofessional territory. Faye is initially skeptical about Don's advances, but he reveals the truth about his past as Dick Whitman when Draper has a panic attack about his identity theft and desertion being discovered by the U.S. government.
Don chokes her to death and hides her body under the bed. It turned out to be only a dream but Don "killing" Andrea was one of Mad Men's most odd and disturbing moments. It also suggests that these affairs and his relationships with women are secrets he wants to bury deep down to never be revealed. Draper is clearly attracted to Lee, a wealthy widow, and they share an intimate plane ride home, but Don turns down her invitation to "share a cab" with Lee when they land in New York. There is an interesting connection that develops between the two in a short span of time.
Amy is one of Megan's friends in California after she left New York and moved to the West Coast to pursue her acting career in Hollywood. After a party at Megan's house, Don's estranged wife invites him to have a three-way with her and Amy. However, there is a sadness to it as if Megan is attempting to make Don feel as though he is happy with her by giving him this fantasy and trying to offer him what he wanted in their marriage.
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