One thing is for sure, Don likes an independent working woman. While housewives and homemakers seem to make him yawn, he loves a woman who is sassy, savvy, and smart. Rachel Menken, business head of her father's department store, is his first intimate romance outside of his marriage. He even tries to convince her to run away to LA with him, but she vehemently declines due to his lack of consideration for his children. Don always has luck on his business trips and engages in a brief fling with a stewardess on a trip to Baltimore.
And before his engagement to Megan, Don gets involved with Dr. Fay Miller, the consumer psychologist that he works closely with. He opens up to her about his sketchy past, and she provides some emotional support. He ultimately breaks things off with her because she admits that she's no good with children. Oh have the tides turned for Mr. Draper!
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