Daniel Randolph Humphrey is a fictional character from the Gossip Girl franchise.
He is one of the core male characters in Gossip Girl, played by American actor Penn Badgley. The character comes from an artistic and musically-inclined family. His father in the show, Rufus Humphrey, is an aspiring rock musician; his mother in the show, Alison Humphrey, is an artist who walked out on her family when Dan was young, leaving him with a deep sense of abandonment and distrust. He has a younger sister in the show, Jennifer Humphrey.
Dan and his family live in Brooklyn, the alternative to the old-money and conservative Upper East Side. The character pursued his education at St. Jude's Preparatory School on the West side as a scholarship student.
Dan Humphrey is considered charismatic and attractive, due to his good looks, charm, and wit. Portrayed as an incredibly talented individual with an interest in poetry, he shares a close bond with his sister, Jenny, evident in his dedication to her schooling and protectiveness of her.
Novel series Daniel Randolph Jonah Humphrey, known as Dan, is a skinny, talented, sensitive, existentialist poet who drinks liters upon liters of instant coffee every day and smokes cigarettes at a frantic pace. He lives in a run-down Upper West Side apartment with his father, Rufus Humphrey — a bohemian, beatnik editor of minor Beat Generation poets — his younger sister, Jenny, who is three years his junior, and their cat, Marx. He has very few contact with his mother, Jeannette, an exuberant hippie artist, since she abruptly abandoned the family home to move to Prague with a wealthy aristocrat.
Dan is a pessimist who often sees the worst in things and is fascinated by death. He is also a romantic whose imagination spirals out of control at the worst possible moments. He has an unfortunate habit of overanalyzing events and his own emotions, which leads him to accumulate a great deal of frustration, as he struggles to manage the gap between reality — so often disappointing to him — and his fantasies. He watches over the people he loves and is particularly protective of his younger sister. His best friend is Zeke Freedman, whom he has known since first grade. At the beginning of the novels series, he's infatuated with Serena and eventually brieftly dates her.
During his senior year of high school, one of his poems (titled Whores) is published in The New Yorker, which leads to him being contacted by a well-known literary agent, Rusty Klein, who then recommends him for an internship with the editor of Red Letter, the most prestigious literary journal in the world.
His primary interest is Vanessa Abrams, though he has not always been a faithful partner to her. He notably cheated on her with Mystery Craze, a poet described as having yellow teeth and an alarmingly thin frame and, later, with Bree, a yoga-lover. For a brief period — despite lacking musical talent — Dan was also the lyricist and singer for the trendy rock band The Raves, before being removed by his guitarist, Damian Polk, after a poor performance at a concert.
Dan attends Riverside Prep (Riverside Preparatory School for Boys) with Chuck, whom he despises. At the end of high school, he receives the E.B. White Writing Award from his headmaster, a prestigious prize recognizing the outstanding creative writing achievements of a Riverside Prep student. After graduation, Dan enrolls in the literature department at Evergreen State College but requests a transfer to Columbia University at the end of his first semester so he can return to New York City to be with his girlfriend, Vanessa. He then completes his undergraduate degree there in the literature program. During this time, another of his poems — titled Serena — is published in The New Yorker and allows him to reconnect with the real Serena. They even start dating again and their romantic relationship will last around two years this time. After finishing his higher education, Dan is admitted to the prestigious Iowa Writers' Workshop in the University of Iowa. In his senior year, he also had a brief homosexual affair with Greg, a colleague from the bookstore where he worked during the summer, before returning once again to Vanessa. By the end of the saga, after a long separation, Vanessa and Dan realize they still love each other and finally confess it.
Dan is described as tall (standing at five feet eleven inches), thin, pale-skinned, with a waxy-looking face, messy black hair, long sideburns and brown eyes.
Television series
The character Dan "Lonely Boy" Humphrey is the son of rocker Rufus Humphrey, and the older brother of Jenny Humphrey. Dan and his family reside in Brooklyn. He is a writer 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.
Season 1 His mother lives away from home, in Hudson, as an artist. Compared to his wealthy classmates at St. Jude's, Dan is financially inferior.
Dan is one of the first people to see Serena back in person. 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 runs into Serena and ends up on a date with her so she does not have to go to the "Kiss On The Lips" party which Blair is throwing. They have a rocky first date and it ends early because he gets a text from his sister in the show saying that she needs help at the party. Serena helps Jenny and saves her from Chuck Bass. Dan is highly embarrassed after this, as at the end of the date he only waves to her from a taxi. He and Serena end up going out again but he leaves her after Blair tells him about Serena and Nate hooking up at a party when Nate and Blair were a couple. They make up and become a constant source of attention.
Behind the scenes is Dan's childhood best friend Vanessa, who is clearly jealous of Serena and very much in love with Dan, but he is oblivious to this. Despite Dan's clear preference for Serena, Serena cannot help but feel jealous of how close Dan is with Vanessa.
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. 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 with, "Okay." She later asks him why he loves her and he reads her the list he made of the reasons. She believes him and says she loves him as well, but she needs to help Blair.
When Georgina Sparks arrives on the Upper East Side with the intent on making Serena's life hell, she gets to know Dan behind Serena's back. Pretending to be "Sarah" and accidentally-on-purpose letting her dog run off its leash in the park, Georgina gets an excuse to talk to Dan. 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 she has slept with someone else and is tired of her holding secrets from him. A few hours after the breakup, he kisses Georgina, thinking she is a helpless girl running away from a psychotic ex-boyfriend. Soon thereafter, Dan is convinced that Georgina is lying to him after being told the truth by Serena. He and Blair manage to fool Georgina into thinking that Dan wants to meet up with her. The real purpose of the plan, though, is to get Georgina to meet with her parents and then get sent to a Christian boot camp. Dan and Serena rekindle what is left of their relationship before Dan ultimately ends it entirely.
Season 2 In the summer, Dan goes from being a lonely boy to a playboy, dating continuously with thoughts of Serena still on his mind. He eventually gets fired from his summer job due to a lack of commitment and heads to the Hamptons hoping to see Serena. However, he finds her kissing Nate and shows anger. He and Serena retreat to talk and spend the night together but decide to keep their relationship a secret. The two rekindle their relationship and talk during a citywide blackout but eventually break up. Dan meets a transfer student named Amanda and starts dating her, leading to tension with Serena. Dan uses Chuck to fuel a new story but later realizes it's wrong to exploit people for art. During a visit to Yale, Dan has trouble getting a recommendation but eventually gets help from a co-ed. Chuck fools a secret society into thinking Dan is Nate, leading to Dan being stripped of his clothes and tied to a statue.
Season 3
Dan joins NYU and quickly fits in among the aspiring writers. He becomes popular, has a short-lived relationship with Georgina, and then moves on to a relationship with Olivia, a Hollywood film star. However, their relationship comes to an end when Olivia returns to Hollywood. Dan confesses his love for Vanessa, who initially turns him down but eventually reveals her feelings for him, and they get together. Dan and Vanessa's relationship is put to the test when Vanessa takes a six-month trip to Haiti for an internship with CNN.
Season 4 The reaction to the Dan, Blair, and Serena triangle on "Gossip Girl" polarized viewers and garnered significant media interest. Some fans appreciated the relationship development between Dan and Blair, finding more chemistry than Blair and Chuck, while others preferred the original Chuck and Blair pairing. Producer Joshua Safran acknowledged that Chuck and Blair would always be connected in their own way and that Dan and Serena would always be connected in their own way. However, he also noted the potential for new roads to be explored that might differ from the initial expectations.
Season 5 The fifth season opens with Dan in the Hamptons. He appears upset when he receives Blair's invitation for her royal wedding. Dan soon finds out that someone has published his book, Inside. Meanwhile, Blair, back from her cruise and is currently in Manhattan again, is frustrated with Louis' domineering mother, who feels the need to have complete control over the wedding. Dan finds out that Vanessa has published his book without his permission and tries to undo the damage, especially after Vanity Fair want to publish a part about Dan and Blair. Desperate, Dan turns to Louis for some help, hoping the prince could put some royal weight on it and manage to cancel the publishing. Louis informs him that he promised earlier to Blair that he's going to take her to the Royal consulate, so he calls her and tells her that he would not be able to make it, much to Blair's disappointment.
Soon after, Blair then arrives at Dan's loft and tells him that despite they haven't spoken since the holidays, she needs a friend to talk to and believes that he is the only one that will truly listen. She announces that she plans to break it off with Louis and asks him about his trip to the Hamptons, to which he responds to staying at CeCe's house.
She asks him to take her there, and Dan tells her he will be there for her for whatever she needs. He decides to conceal the real reason why Louis couldn't make it. Just as they were about to make a move, Louis enters the loft. Blair assumes that he was following her and starts reprimanding him until Dan's conscience gets the better of him and reveals that Louis was only helping him with his book issue. Blair soon becomes furious with Dan as he did not tell her the real reason why Louis could not make it and departs with Louis, arm-in-arm, leaving Dan alone and heartbroken. At the end of the episode, it's revealed that Blair is the one pregnant.