Dan Humphrey

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.

The love of his life is Vanessa Abrams, though he has not always been the best boyfriend to her. He notably cheated on her with Mystery Craze, a poet with yellow teeth and an alarmingly thin frame and, later, with Bree, a yoga-lover. For a brief period — despite having no musical talent whatsoever — Dan was also the lyricist and singer of the trendy rock band The Raves, before being kicked out by his guitarist, Damian Polk, after a pitiful 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.

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.

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.

Over the next few episodes, Blair is found having trouble keeping the pregnancy a secret and begins having morning sickness. Things get more difficult when Louis's sister, Princess Beatrice, comes to town. When she hears Blair's morning sickness in the bathroom, she begins to assume that Blair has gone back to being bulimic. She decides to invite Blair to a feast to be sure.

Meanwhile, in Brooklyn, Dan is still trying to stop the publishing of his book to save the relationship he has built with his closest friends and family. He calls Serena on the phone and asks her how she went through Lily's bank account so that he can go to Vanessa's bank and look for the publisher. However, she tells him that it was all Chuck's doing, driving him to go searching for Chuck. To his horror, he finds Chuck getting beat up by men. He attempts to save Chuck, when he reveals that the men were not real criminals, and he paid them to hurt him, much to Dan's astonishment. This leads Dan to search for Blair and inform her about Chuck's recent dilemma.

Season 6

In Season 6, Dan tells Serena that the reason he didn't give her an answer to the "I love you" was because it was easier to focus on his anger at Blair, than to face the possibility of getting what he always wanted in the fear of losing it again. Dan also solidifies his love by telling Georgina and Rufus that he had a plan all along to win and that there is no winning without Serena.

In the finale, Dan reveals to Serena their first meeting at a party, where Dan first spoke to her and fell madly in love. Dan realized at that party that he could never pull Serena out of her world but he couldn't give up either. He realized that the only way he could get Serena was to write himself into the Upper East Side drama by using a blog to create a legend; the blog came to be known as Gossip Girl. Serena was overjoyed at the revelation, stating that Dan, through Gossip Girl, had written her and everyone else a seven-year love letter and made her realize that she belongs on the Upper East Side with Dan.

Five years later, Dan and Serena get married, surrounded by their closest friends and family.

2021 sequel series

Dan does not appear in the 2021 sequel series but his Gossip Girl blog is featured in the first episode when Kate Keller finds it and decides to relaunch it on Instagram. In the episode "How to Bury a Millionaire" from season two, Georgina reveals that he lives in Brooklyn Heights and is still married to Serena. Georgina also revealed that the couple has a kid.

Reception

Dan Humphrey’s character has garnered much media recognition. Alfonso Espina of The Huffington Post declared that Dan was the “Nick Carraway character we viewers could live vicariously through.” Jason Gay of Rolling Stone praised Badgley’s characterisation, claiming that “while another actor may have played Dan as a blah straight man, Badgley imbued him with an occasionally obnoxious know-it-all-ness.” The New Yorker cited Dan as “the token-boho character”; while, New York Magazine described Badgley’s Dan as “the moralistic outsider, or what passes for one on a show produced by the guy who created The O.C.”. Jarett Wieselman of Entertainment Tonight asserted that “charming and disarming in equal measure, Badgley's incarnation of the Brooklyn-boy gone bad was always a comedic and emotional highlight.”

Other colleagues have also commented on Dan Humphrey’s character. Blake Lively, Badgley’s co-star, declared that "Dan was supposed to be the goofy, nerdy guy who felt like he never measured up to other people, but Penn [Badgley] decided to play it a little more arrogant. Like he's smarter than these spoiled little brats." The series executive producer, Stephanie Savage, claimed that “as he [Dan Humphrey] is the outsider, he's somebody who when he's pointing out what's absurd about the world, you have to believe he's smart enough to get it and also deliver it in a way that you find it kind of amusing and not just critical or judgmental.”