Daniel Humphrey

General Information
Dan "Lonely Boy" Humphrey is the son of rocker Rufus Humphrey, and is the older sibling of Jenny Humphrey. Dan is a poet and attends the St. Jude’s School for boys with enemy Chuck Bass. 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 in a way. Dan and his family reside in Williamsburg, Brooklyn, and he wishes to attend Dartmouth College. After him & Serena broke up, Dn went on a mass dating spree to try & trick himself into thinking that he was over Serena.

Relationships
• Serena van der Woodsen
    • Start Up: Pilot (101)
    • Broke Up: Woman On the Verge (117)
        • Reason: Serena lied to Dan and told him that she cheated on him.

• Georgina Sparks
    • Start Up: Woman on the Verge (117)
    • Broke Up: Much "I Do" About Nothing (118)
       • Reason: Dan learned the truth about Georgina.

Differences in the book & show
• In the book series, he is described as shaggy, unshaven most of the time, and kind of "nerdy". In the TV series, he has very short hair and is clean shaven.

• In the book series, he attends Riverside Prep on the Upper West Side with wealthy playboy Chuck Bass, while "Waspoid" lacrosse player Nate Archibald attends St. Jude's; in the TV series, all three attend St. Jude's.

• In the book series, he dates Serena only for a brief period of time; in the TV series he dates Serena through a span of months.

• In the book series, Dan loses his virginity to Vanessa; in the TV series he loses it to Serena.

• In the book series Dan was a heavy smoker; in the TV series he doesn't smoke at all.

• In the book series, his family resides on the artistic Upper West Side; in the TV series they reside in rock palace Williamsburg, Brooklyn.

• In the book series, he wasn't long time best friends with Vanessa Abrams, since in the books she just moved to NYC from Vermont when she was 15, he is disinterested in her in the first book, because he's always eyed sexy Serena van der Woodsen.

• In the book series, Dan briefly experimented with his sexuality by dating a man. In season one of the television series, he only dates Serena van der Woodsen and sees Georgina Sparks.