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Sign up Log in. Sara Underwood Nude Portland, Oregon is the native city of Sarah Jean Underwood, where she was born in After school, Underwood enrolled at the University of Oregon and studied at the University of Portland. Entering adulthood, Underwood worked as an assistant seller of building materials and then worked in Beaverton, Oregon at the Hooters chain of restaurants. In October , the girl hit the pages of Playboy magazine for the first time, including appearing on the cover. Then in the July issue of , Underwood was named Girlfriend of the Month.