Dan "Lonely Boy" Humphrey is the son of rocker Rufus Humphrey, and is the older sibling of Jenny Humphrey. His best friend is Vanessa Abrams, whom he had feelings for a year prior to the pilot episode of Gossip Girl. Dan is a poet and attends the St. Jude's School for boys. 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. He has somewhat of a disgust for Serena’s best friend, Blair Waldorf; though, he seems to have warmed up to her given their heart-to-heart in "Bad News Blair". Dan and his family reside in Williamsburg, Brooklyn, and he wishes to attend Yale College.