He is described as being attractive and sensitive, loves to write poetry, and one of his poems, "Sluts," was featured in The New Yorker.
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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 considered to be an intellectual when it comes to writing and literature, and was in fact an intern for The Strand one summer.
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.
Dan later realizes that he has feelings for Vanessa, so he begins a relationship with her.
They have a fight when a video of Jenny without her pants is leaked onto the internet, and she apologizes by sending his poem to The New Yorker. He gets an agent called Rusty Klien who claims he is "the next Keats." Rusty introduces Dan to Mystery Craze, a novelist.
Dan and his family live in Brooklyn, New York, the alternative of the old-moneyed and conservative Upper East Side. 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 breaks up with Greg, who becomes Chuck's boyfriend instead. He went to The Evergreen State College for bachelor studies. He has longed for Serena van der Woodsen since a party when they were fifteen and she was the only person who was nice to him.
Dan "Lonely Boy" Humphrey is the son of rocker Rufus Humphrey, and is the older sibling of Jenny Humphrey. During the beginning of the show Dan has had somewhat of a disgust towards Serena's childhood best friend Blair Waldorf, however as the seasons progressed he develops a close friendship with her.
He is one of the central male characters in the television adaptation of the same name, where he is portrayed by Penn Badgley.