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Behind the scenes, though, is Dan's childhood best friend Vanessa, who is clearly jealous of Serena and very much in love with Dan. Despite Dan's clear preference for Serena, Serena cannot help but feel jealous of how close Dan is with Vanessa, such as when Dan tells Vanessa that his mother came home, while Serena learns this from Vanessa instead of Dan himself.
When he learns from the Gossip Girl site that Serena was seen buying pregnancy tests he freaks out knowing that the child could very well be his as they've slept together.
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. 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.
His favorite past time is writing on his black journals. Jude's Preparatory School for Boys, on the Upper East Side, with Chuck Bass and Nate Archibald.He accidentally bumps into her, causing her to fall and spill the contents of her purse and leave behind her cellphone.In an attempt to see her again, he returns the phone to The New York Palace Hotel where she lives.He is one of the central male characters in the television adaptation of the same name, where he 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.