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She’s the anti-Betty, a bohemian artist who doesn’t want to be domesticated, throwing a TV set he’s gifted her out the window of her Greenwich Village apartment and eventually turning down his marriage proposal. RELATED: Bryan Cranston Gave Jon Hamm Advice for Saying Goodbye to Mad Men Rachel Menken (Maggie Siff) The no-nonsense, sophisticated Jewish department store heiress demands Don up his game if he wants her business.An early challenge to his ideas of a woman’s place in the world, naturally, he tries to seduce her!When Jimmy insults the Utz owner’s wife, Don tries to do damage control with Bobbie, but she puts the moves on him, suggesting Jimmy will apologize if he knows “he's got a shot at your wife.” Later at the apology dinner, she tries to shake Don down for ,000 in the ladies’ room.His response: grabbing her and putting his hand up her skirt, and threatening to ruin Jimmy if he doesn't apologize before the main course.Faye is the total package: smart, beautiful, independent and no pushover. It’s a tad Freudian: Don reminds her of her father, “a handsome two-bit gangster like you.” Don does let his guard down with her, revealing his true identity.But Don likes a challenge, so even the woman with a Ph. And she goes against her ethics, setting up a meeting for him with Heinz, because she knows they’re unhappy with their agency.
Candace (Erin Cummings) Don spends his first post-divorce Thanksgiving at his new apartment with Candace, a prostitute whom he pays to slap him around. Later, he and account man Lane will hook up with her and her friend Janine at a nightclub. But try as she might to remain professional, Allison soon loses it during a focus group where the secretaries talk about their love lives as Don looks on.“That poor girl,” Betty says of Don’s second wife, Megan.“She doesn’t know that loving you is the worst way to get to you.” Midge Daniels (Rosemarie De Witt) Midge is the first lover of Don’s we meet in the pilot, even before we learn Don’s a married man. Years later, she turns up addicted to heroin and Don takes pity on her and buys one of her paintings.He also knows the effect she’ll likely have on Betty after they unexpectedly run into her and Henry.Alice (Amy Motta) and Doris (Becky Wahlstrom) Don ties one on at the 1965 Clio advertising awards ceremony, taking home a statuette and Alice, who’s sized him up at the bar and asked Roger whether he’s single.
WATCH: Jon Hamm Says Don't Count on a 'Mad Men' Movie Aimee (Megan Ferguson)Don’s sexual issues make slightly more sense when you take into account where they started: Dick Whitman (Draper’s original identity) is “a whore’s child,” as his stepmother liked to remind him, who lost his virginity as a terrified teenager to Aimee, a prostitute in his uncle’s brothel.