Paul Kinsey (Michael Gladis): A creative copywriter and Princeton University alum, the pipe-smoking Paul prides himself on his politically liberal views. At some indeterminate time, he had a relationship with Joan Holloway which ended badly, largely because Paul talked about it too much. Paul tried unsuccessfully to date Peggy soon after she was hired by Sterling Cooper. Through most of the second season, Paul dated Sheila White, an African-American woman from South Orange, New Jersey. They broke up while in Oxford, Mississippi where they had gone as Freedom Riders to oppose segregation in the South. It is a source of pride for Kinsey that he lives in the low income southern section of Montclair, New Jersey.
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