Entertainment Fuse, writes "It’s not easy being Don Draper. In the latest episode, "The Collaborators," we learn new information about Dick Whitman’s past and gain some insight into how the young man transformed himself into the Don Draper we now know."
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The reason don sleeps with woman is that they admire him to a point where he can feel good about being who he is. This is why he chose megan over the doctor woman, who really knew him. It isn't about sex, its about reaffirming his fake identity. All his mistresses really adore him. When they get old, he moves on to another woman who wants him. Peggy and joan don't see him that way.