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Dan Humphrey

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Dan Humphrey
Gossip Girl character
Portrayed byPenn Badgley
First appearanceBook Series:
Gossip Girl
TV Series:
"Pilot"
Last appearanceBook Series: Don't You Forget About Me
Created byCecily von Ziegesar
In-universe information
Other namesD
OccupationBook Series:
Poet
College Student
TV Series:
High School Student
FamilyBook Series:
Rufus Humphrey (father)
Jeanette Humphrey (mother)
Jenny Humphrey (sister)
TV Series
Rufus Humphrey (father) Alison Humphrey (mother)
Jenny Humphrey (sister)

Daniel Jonah Humphrey, or simply known as Dan Humphrey, is a main character in the best selling Gossip Girl book series. He is portrayed by Penn Badgley in the TV series.

Book Series Background

Daniel Humphrey is the son of Rufus Humphrey and has a younger sibling, Jenny Humphrey. His absent mother, who ran off with a European aristocrat, returns to support Dan when she hears of his sexual confusion. Dan and his family live on the liberal cultured and artistic Upper West Side, the alternative of the old moneyed and conservative Upper East Side. He attends the Riverside Preparatory School for Boys, where wealthy playboy Chuck Bass attends, on the West Side as a scholarship student. At the end of the series, he matriculates to Evergreen State College in Washington.

He is described as being very 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 and chain smokes cigarettes. 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.

Overview

Dan has had the longest unrequited love for Serena van der Woodsen since their pre-teen years. When Serena tried out for Vanessa's film Dan is a part of, Dan and Serena's romantic engagement starts there. At the end of the first novel, Serena saves Jenny from being further molested by Chuck Bass. In the second-third novels, Dan begins falling for Vanessa Abrams and Serena's lust for Blair's wealthy step brother Aaron Rose proved too much for the couple, and they call it quits.

Dan and Vanessa dated for a while, until he cheats on her with a cute yoga girl. To make matters worse after the two break it off, Vanessa moves into Jenny's old room. But a same-sex situation with a geeky kid named Greg makes Dan question his sexuality. Greg and Dan date for a while, but Greg leaves Dan for Chuck Bass, the two appearing to be having a fling at Blair & Serena's farewell party. At the end of the series, Dan concludes he's not gay, but was merely a questioning youth and tells Vanessa he loves her.

Dan's a talented poet. His poems seem to be mostly romance and darkness centered at times, and his great talent got him published in the New York Observer. At the beginning of the first book, Dan expresses a brief interest in Columbia University in the City, but ends up at the end of series matriculating to Evergreen State College in Washington.

Dan's mother left him when he was young for a European aristocrat, which is what probably caused his dad's hostility toward high society. His mother returns to NYC at the end of the series, and supports Dan's supposed homosexuality, even enrolling in PFLAG and buying Dan homo-erotic poetry and novels.

TV Series Background

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 given their recent heart-to-heart in Bad News Blair. Dan and his family reside in Williamsburg, Brooklyn, and he wishes to attend Dartmouth College.

Season 1

Dan has liked Serena since they were 15 when Serena was the only person who spoke to him at a party, but he's never really spoken to her before. He lives with his father, Rufus Humphrey, and younger sister, Jenny Humphrey, in Brooklyn, New York. His mother lives away from home, in Hudson, as an artist. He is financially strained compared to his wealthy classmates at St. Judes, such as Chuck Bass, the party boy whom Dan hates the most.

Dan was one of the first people to see Serena back in person. He accidentally bumped into her causing her to fall and spill the contents of her purse, leaving behind her cellphone. In an attempt to see her again, he returns the phone to The New York Palace Hotel where she lives. He runs into Serena there and ends up on a date that with her so she wouldn't have to go to the "Kiss On The Lips" party which Blair is throwing. They have a rocky first date, going to his dad's concert. The date is ended early because he gets a text from Jenny saying that she needed help at a party. Serena came along and helped save Jenny from Chuck. The next morning Dan was freaking out over his embarrassing good bye, a wave. They end up going out again but he leaves because Blair told him about Serena sleeping with Nate, while he was dating Blair. They make up and become a constant source of attention.

At the Ivy Mixer, Blair tells the whole school and Ivy scouts that Serena is a patient at the Ostroff Centre, presumably for alcoholism. Serena then goes on stage and lies to protect the real patient at the Centre: her brother. Dan is surprised at Serena's apparent problem, especially after it seems that Serena has been making a real effort to change from her old partying ways. However, Jenny Humphrey reveals that Eric is the actual patient, which then causes Dan to respect Serena for protecting her family as he says that it was "cool" what she did up there on stage. This event actually strengthens their relationship, instead of weakening it like Blair had intended it to do.

Behind the scenes, though, Dan's childhood best friend Vanessa is there, who is clearly jealous of Serena and very much in love with Dan. Dan is oblivious to this. Despite Dan's clear preference for Serena, Serena can't 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 Gossip Girl that Serena was seen buying pregnancy tests he freaks out knowing that the child could very well be his as they've slept together. His father sees this as well and is extremely upset that his son may be a teenage father. Dan explains he will stay with Serena no matter what she does because he loves her. He tells this to Serena who says she's not having a child. Later on, he tells her that he loves her, and she responds "OK" which is not the response he was looking for. She later asks him why he loves her and he tells her a list he made with the reasons. She believes him and says she loves him as well, but she needs to go to help Blair. When he asks why, she says "one of the many reasons you love me."

Upon Georgina's arrival in the Upper East Side, she tries to get to Serena as much as possible. One of these ways is by getting to know Dan behind her back. Dan meets Georgina when her dog runs up to him. She announces herself as Sarah. It is later seen that Dan and Vanessa have taken "Sarah" under their wing as they believe she is a new girl to the Upper East Side who doesn't know her way around.

Eventually, Dan breaks up with Serena, because he believes that she has slept with someone else and he is tired of her holding secrets from him. A few hours after he breaks up with Serena, he kisses Georgina, believing that she is a helpless girl who is running away from a psychotic ex-boyfriend. Soon thereafter, Dan is convinced that Georgina is lying to him by being told the truth by Serena, as something like that "doesn't roll off the tongue". He and Blair manage to fool Georgina into thinking that Dan would like to meet up with her. The real means of the plan, though, was to get Georgina to meet with her parents and then get sent to a reform school. Dan and Serena rekindle what is left of their relationship before Dan ultimately ends it entirely. He is last seen spending some time with Vanessa during the start of the summer holidays.

Season 2

According to Gossip Girl, over the summer Dan went from "Lonely Boy to Playboy". Dan occupied himself by having continuous dates throughout the summer, with Serena still on his mind. Due to Dan's emotional complications, he is unable to complete an essay he was to submit. This ultimately results in his being fired due to his lack of commitment. Upon being fired from his summer job, he heads to the Hamptons upon realising that he has been missing Serena. He hopes that by seeing Serena he will realise that they made the right decision, and he can move on. He arrives in the Hamptons, at the annual White Party, to find Serena and Nate in a passionate kiss. This reveals his true feelings for Serena as he shows obvious anger towards Serena's "cheating". Serena tries to convince him that she kissed Nate so as to make an anonymous woman [to Dan] jealous. Dan goes to leave, when he is confronted by a pair of girls he had dated throughout the summer. The girls, having found out about one another's relationships with Dan, pour their drinks on Dan and leave. Having been caught out by Serena for his hypocrisy, Dan and Serena retreat into the house to talk. They decide to meet up later at the beach, where they spend the night together.

The following morning, Serena and Dan decide to halt any discussions on their relationships until they are back in the city. After some confusion between who was to take the train and who was to take the bus, they both ended travelling back to the city on the bus. This creates tension between the two, and as Serena gets up to use the bus bathroom, she trips and falls on Dan. She pulls up Dan and the two go into the bathroom to "fool around". The two decide to keep their rekindled relationship a secret until they were sure of themselves. Back in the city at Blair's "Welcome Back" party, Nate discovers the two in an embrace, revealing publicly that their relationship is "back on".

Differences between book and TV series

  • 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.

Relationships

Book Series

TV Series

First Relationship:

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

Second Relationship:

    • Start Up: Summer Kind of Wonderful (201)
    • Broke Up: The Dark Night (203)
      • Reason: They realized that Serena could never live up to the image that Dan has of her, and that she just wants to be herself.


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