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  • Dan Humphrey is a fictional character in the best selling Gossip Girl book series. He is one of the main male characters in the television series of the same name and is portrayed by Penn Badgley. Dan Humphrey is the son of Rufus Humphrey and has a younger sister, Jenny, while his mother remains absent for the majority of the series. Dan and his family live in Brooklyn, New York, the alternative of the old-moneyed and conservative Upper East Side. He attends St. Jude's Preparatory School for Boys on the West Side as a scholarship student. His life changed dramatically when his father, Rufus Humphrey, married the wealthy Lily Van der Woodsen, moving the family to the Upper East Side. He is described as being attractive and sensitive, loves to write poetry, and one of his poems, "Sluts," was featured in The New Yorker. He revealed his favorite word is death and drinks copious amounts of dark coffee. He over analyses and is easily frustrated. Dan is very close and protective of little sister Jenny who attends an exclusive private school, called the Constance Billard School for Girls, a small, elite, all-girls school located at 93rd and Madison Avenue.