Dan Humphrey

Dan Humphrey
Gossip Girl character
Penn Badgley as Daniel Humphrey
First appearance	Novel: Gossip Girl (Book 1) Television: "Pilot" (episode 1.01)
Created by	Character Cecily von Ziegesar Developed for Television Josh Schwartz Stephanie Savage
Portrayed by	Penn Badgley
Information
Full name	Daniel Randolph Humphrey
Nickname(s)	Television: Cabbage Patch (by Blair Waldorf) Humphrey (by Blair Waldorf) Labrador (by Blair Waldorf) Lonely Boy (by Gossip Girl) Brooklyn (by Chuck Bass)
Aliases	D D.H.
Occupation	Novels: Poet High school student (at Riverside Preparatory; graduated) College student (at Evergreen State) Television: Author Freelance writer High school student (at St. Jude's; graduated) College student (at New York) Former W Magazine Intern

Daniel Randolph "Dan" Humphrey is a fictional character in the best selling Gossip Girl book series. He is the main male character in the television series of the same name and is portrayed by Penn Badgley. Daniel Humphrey is the son of Rufus Humphrey and has a younger sister, Jenny Humphrey. His absent mother, who ran off with a European aristocrat, returns to support Dan for a while. 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 St. Jude's Prepatory 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 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. 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.

Novel series

Dan Humphrey lives with his father Rufus, and sister Jenny in Brooklyn. He is tall and pale, and is quite neurotic. He enjoys drinking coffee. He is considered to be an intellectual when it comes to writing and literature, and was in fact an intern for The Strand one summer. His favorite past time is writing on his black journals. He goes to St. Jude's Preparatory with Chuck Bass and Nate Archibald.

In the first part of the books, he is in love with Serena Van Der Woodsen because of a party he threw at their apartment before he went to boarding school. When Serena returned to the Upper East Side, she was ostracized by her peers, so she made friends with Dan and Jenny. Dan later realizes that he has feelings for Vanessa, so he begins a relationship with her.

They have a fight when a video of Jenny without her pants is leaked onto the internet, and she apologizes by sending his poem to the New Yorker. Dan gets published, and they make up. He gets an agent called Rusty Klien who claims he is "the next Keats." Rusty introduces Dan to Mystery Craze, a novelist. They hook up on stage at a poetry reading which Vanessa sees, effectively ending their relationship. He gets an internship at Red Letter, which he leaves once he realizes they don't want him there for his talent.

He gets back together with Vanessa after he sends her a small, pink singing toy from Japan to film, and at a party at her house, a band called The Raves make him their new front man because of his poems, which they thought were lyrics. He hooks up with one of the instrumentalist's wife, which ends his stint with them. He later meets Bree while working at The Strand one summer while he was still dating Vanessa.

Dan explores his sexuality later in the books by starting a relationship with his co-worker in the Strand by making literary salons with him, which were, in actuality, giant orgies. He breaks up with his co-worker because of Chuck Bass, and he realizes that he truly loved Vanessa. He went to The Evergreen State College for bachelor studies.

TV series

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, who is secretly in love with him. Dan and his family reside in Brooklyn. He 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. On the beginning of the show, he has somewhat of a disgust for Serena’s best friend, Blair Waldorf; however by the end of the third season, Dan and Blair have warmed up to each other, to the point that Dan comforts Blair after her breakup with Chuck. In the fourth season, he develops romantic feelings for Blair, but hides it.

Season 1

His mother lives away from home, in Hudson, as an artist. He is financially strained compared to his wealthy classmates at St. Jude's.

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 there and ends up on a date that 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, going to his dad's concert. The date is ended early because he gets a text from Jenny 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 sleeping together when Nate and Blair were a couple. 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 reveals that Eric is the actual patient, which then causes Dan to respect Serena for protecting her family. This event actually strengthens their relationship, instead of weakening it like Blair had intended it to do.

Behind the scenes, though, is Dan's childhood best friend Vanessa, 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 cannot 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 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." 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 of the reasons. She believes him and says she loves him as well, but she needs to help Blair. When he asks why, she says "one of the many reasons you love me."

When Georgina Sparks arrives at the Upper East Side, 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, giving her 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 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. He and Blair manage to fool Georgina into thinking that Dan would like 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 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 realizing that he has been missing Serena. He hopes that by seeing Serena he will realize 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 Archibald 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 Nate's girlfriend (an older, married woman who was also paying him for being with her) 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 traveling 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".

In "The Dark Night" during the city-wide blackout, Dan and Serena talk about their problems while they were both trapped in an elevator. After a long talk (and a bit arguing), they realized they keep having the same fight, and break up.

During their return to school, Serena and Dan are now friends until he meets a transfer student named Amanda Lasher. They share the same interests and have perfect chemistry. Blair attempts to keep them separate by making her one of her entourage so that Serena wouldn't have to suffer seeing them together and so she also wouldn't have to lose the competition of rebounding. Serena meets Amanda and nearly makes a fool out of herself. Blair forces Amanda to join them for lunch. Dan, thinking that Serena is trying to keep him away from Amanda gets Serena, who was reasoning with Dan why it happened, irritated when he kept implying that she was the one who forced her to lunch. Dan and Amanda's relationship goes public much to Serena's irritation. Serena then invites Dan and Amanda to go out later that night which turns into as disaster as Dan and Amanda continue to make her feel out of place. Isabel and Penelope, after witnessing Dan go out with Amanda that led to the relationship getting public, offers Serena several suitors, one in particular is a Dalton lacrosse team captain. Serena's new suitor fails to impress Dan. Dan thinks that Serena used the lacrosse team to rub it into his face. Later on, Penelope ruins Amanda's hair with a little help from Chuck. Dan runs to Amanda's aid who brushes him off saying that she no longer wants to see him. Dan gets into an argument with Serena and leaves. The next day, he is shunned because of Serena's rise to Queen Bee status.

Dan's recommendation from Noah Shapiro, a writer, leads him to find new inspiration in the form of Chuck Bass. Noah suggests he use Chuck to fuel a new story. Dan does so and loses his shoes in the process. He ends up creating the character of 'Charlie Trout', a character that impresses Noah and asks him to find out what makes him tick. That night, Chuck mistakes a woman of being a prostitute and nearly gets punched until Dan defends him. The two end up in jail and Chuck confesses that he thinks his father hates him because he thinks he killed his mother at Chuck's birth. Chuck gets out a jail with some help from his lawyers and discovers Dan's reason as to why he was hanging out with him. Chuck gets angry at Dan and leaves him, saying that he lied about his mother's death and that she died in the Andes in a plane accident. Dan calls Noah Shapiro who bails him out. Dan confesses that he thinks it's wrong to exploit people for art and that he'd rather be safe. The two part ways and in bad terms.

During a visit to Yale, Dan's recommendation for Yale admission goes awry as his only recommendation came from J.L. Hall. Jeremiah Harris and Noah Shapiro likely declined to write for Dan's recommendation. The Dean of Admissions suggests that he find someone to read his work. Dan then finds out Nate used his name to get into a fling with Jordan, a co-ed girl who eventually helps Dan get his work to other literature professors. Dan is stripped of his clothes and tied to a statue by members of the Skull & Bones after Chuck fools them into thinking he is Nate. Chuck's revenge on Dan then backfires on Chuck who loses Nate as a friend after Nate finds out about what he did to Dan.

Dan and Nate begin a friendship much to Chuck's chagrin. During an invite to play soccer, Dan tries to visit Nate at his house and finds out about Nate's financial situation. Nate has been squatting in his own house that got seized amongst other property of the Archibalds. Dan invites Nate to a family dinner and tells Nate that he knows about Nate squatting in his own house. Nate leaves angry. Rufus talks to Dan and tells him that Nate needs help even if he doesn't want it, seeing as Nate has no one to turn to for help. Dan finds Serena outside Nate's house and repair their relationship. The two become friends. Dan convinces Nate, who moves in after his house got seized.

With Blair's situation with Chuck now out of hand, Serena gets Dan to help Blair and tells her that wearing him down would help her situation. Later on, he continues to help Blair by telling her that she should intercept him at home. With Blair desperate, he tells Blair that she should take a risk and say those '3 words, 8 letters' anyway. During Aaron's opening at Rufus' gallery, Vanessa confesses that Blair and Chuck used her in one of their sick games. Dan ruins Blair's opportunity to tell Chuck that she loves him and tells Serena what happened. He said that the two were bound to break up eventually and that what they did to Vanessa was sick. Serena says that Vanessa's matter is different and that Chuck and Blair do love each other. He later apologizes to Serena and get into an honest conversation. Serena confesses her feelings for Aaron and Dan gives her his blessing to date other people.

Aaron and Serena start to date each other while Dan realizes that he still has feelings for Serena. Aaron has been concerned that Serena leans emotionally more on Dan than him. He asks her to come with him to Buenos Aires for Christmas. Serena asks Dan for his opinion, and he tells her to go. At Eleanor's wedding however, Dan confronts Serena about his feelings for her. Because she knows about her mother and Rufus' relationship, and because she has already said yes to Aaron, Serena turns Dan down and goes ahead with Aaron's trip. Serena breaks up with Aaron during the holiday and Dan and Serena meet with each other and they both decide there are better off back together. Dan soon learns he shares a sibling brother with Serena and becomes ridden with guilt when Rufus asks him to let Lily tell Serena the news.

Serena and Dan attempt to return to normal, but find this difficult with Lily and Rufus, who have decided to go public with their relationship. Dan, and Serena both get acceptance letters to Yale but Serena decides that Yale isn't for her and applies to Brown and gives her spot to Blair who was wait-listed. A new teacher named Ms. Carr teaches at Constance Billard and there is an obvious attraction between them. Blair is so willing to get back at Ms. Carr for giving her a B on a paper that she sends in a rumor to Gossip girl concerning a secret relationship going on between Dan and Ms. Carr. Serena herself is becoming suspicious when she sees Dan and Ms. Carr discussing Dan's paper together but believes Dan when he says nothing is going on between the two of them. Serena then sees Dan and Ms. Carr in a coffee shop together. She cannot hear what they are saying but in fact Dan is only comforting Ms. Carr who is in tears about the slanderous teacher-student relationship rumor. Serena captures a photo of Dan touching Ms. Carr's face in an intimate way and shares the photo with Blair although she has doubts about the authenticity of the situation.

Blair enters a parent-teacher meeting at Constance Billard and presents the incriminating photo at hand. Dan explains to Serena nothing happened between him and Ms. Carr but it is too late. Ms. Carr is fired. Serena and Dan's relationship hits another dead end when things become too much for them to take. First their parents start dating, then they find out they shared a half brother together, and now the mess of the rumor.

Serena goes to apologize to Ms. Carr while admitting regretfully that she was the one who gave the photo to Blair. Later Dan visits Ms. Carr and starts to apologize for how things went down but then she kisses him. Dan, at first, is surprised at her actions. Ms. Carr points out that she doesn't teach at Constance anymore so there is no student-teacher relationship. So Dan obliges and they have sex in the dark of the room.

Season 3

Dan joins Blair, Vanessa and Georgina at NYU and instantly fits in amongst many aspiring writers. His stay at NYU also tests his friendship with Vanessa, who assumes that Dan has been absent in their friendship ever since he became wealthy. Dan explains to Vanessa that he and his family are still adjusting to their nouveau-riche status and Vanessa leaves frustrated at Dan.

Dan's first day at NYU reveals Georgina Sparks' return. When Georgina throws a party, Blair's attempt at sabotage results in Dan standing up for Georgina. Dan is popular at NYU, and his influence leaves Blair ostracized.

Dan and Georgina's relationship is short-lived in the episode "The Lost Boy". Georgina sends Blair on a wild goose chase to enter an elite secret society that gets her into a bidding war with Chuck Bass at an auction. Serena recognizes Georgina's handwriting in Blair's invitation to the secret society and confronts her. The Humphrey family leaves and Georgina is left alone at the auction. Serena reveals Georgina's scheming to Dan and Dan ends his relationship with Georgina. Georgina leaves for Boston when she discovers that Scott, Vanessa's boyfriend, is Rufus and Lily's love-child and that Vanessa had known that he was for a long time.

In "Dan de Fleurette", Dan moves on from his relationship with Georgina when he meets Olivia, a movie star who attended NYU to be a normal college student. Dan first meets Olivia, who calls herself Kate until her movie premiere of Fleur reveals that she is Olivia Burke, a Hollywood movie star. Olivia apologizes to Dan and they embark in a new relationship.

Georgina's return from Boston has her blackmailing Vanessa when she discovers that Dan has moved on from their relationship so quickly in "Rufus Getting Married". Dan, then persuades Vanessa to reveal her secret, only to find out that Scott Rosson is his half-brother, the love-child of Rufus and Lily. Rufus and Lily's wedding has Dan and Vanessa reluctant to tell the truth about Scott. On Rufus and Lily's wedding when Lily gets cold feet, Rufus confronts her with Scott unknowingly asking if their wedding was off. Lily scolds Scott and Georgina reveals that Scott is their love-child. Dan arrives with the rest of the family and confirms Georgina's statement. Dan and Blair find Georgina eating the wedding cake and Blair leaves. At the end of the episode, Dan expresses regret that Georgina left unscathed. Blair assures him that she didn't by sending Dorota and Vanya to get rid of her.

Dan and Olivia encounter several troubles in their relationship when Vanessa alienates them both during her attempt at getting the freshman toast at NYU. When Dan introduces Olivia to Rufus and Lily, she starts acting like a stereotypical movie star towards them until Vanessa reveals that she lied to the both of them so that Olivia wouldn't have to meet her judgmental mother, Gabriela. Vanessa loses the toast to Olivia and properly reintroduces Olivia the next morning after the incident. Olivia's movie star background also catches up to her when she is forced to continue her fake relationship with Patrick Roberts, her former co-star. Serena intervenes and Dan and Olivia soon manage to make their relationship public.

Dan and Olivia's relationship soon comes to an end when Olivia is again forced back into the world of film and return to Hollywood but not without Dan and Vanessa giving her the best college experience. The college experience results in a threesome that consequently leads to Dan and Olivia's break-up when Olivia states that Dan has feelings for Vanessa. Vanessa unfortunately, falls for theater student, Paul Hoffman.

With Olivia gone, Dan confesses his love for Vanessa during the anniversary of Bart Bass' death but Vanessa turns him down. Dan attempts to impress Vanessa by impressing Gabriela that ends with Gabriela telling Dan that if he breaks Vanessa's heart, their friendship wouldn't make it. Vanessa eventually reveals her feelings for Dan at a beach party when Dan arrives with a fresh date and Vanessa gets back together with Paul Hoffman. Dan had been unaware that Vanessa had ended her relationship with Paul until Paul and Dan's date reveals each others' predicaments, get together and leave Dan and Vanessa at the party. Dan and Vanessa reveal their feelings toward each other and kiss at the end of the episode.

Dan finds little trouble with his relationship with Vanessa and reveals their relationship to Rufus. Vanessa, frustrated at the lack of something different in their relationship, heeds Nate's advice on role-playing and sets up a date fashioned according to Dan's favorite movie Rear Window. Vanessa is not convinced that Dan appreciates what she did for her date, and she leaves. Dan confronts her and tells her that their relationship is different from their friendship.

Dan applies to get into Tisch's writing program as Vanessa reads and secretly critiques one of the stories that he plans on submitting for admission. Dan secretly read Vanessa's film script and is impressed, unaware that Vanessa is also applying for the same program.

Towards the end of the season, Vanessa decides to accept an internship with CNN, that of which requires her to go on a six month trip to Haiti. Despite this, the two of them decide that they can still maintain their relationship as a long-distance one.

In the season finale, Dan wakes up with Serena in his bed. The viewers learn that the two did not sleep together but - after staying up until 4AM talking and drinking wine - they shared a kiss, that of which Serena classifies as them "falling into a comfortable path for one...or ten minutes". When Dan hears that Serena breaks up with Nate, he calls her, possibly to say he had feelings for her. When she announces she won't be back to talk to him till September he appears very disappointed. He then shuts the e-mail he had opened to write to Vanessa, his current girlfriend, who is no longer taking his calls (due to Nate's interception after finding out from Gossip Girl's blast and later overhearing at the hospital about the kiss). When he later learns that Serena is going to Paris with Blair, he goes online to book a ticket. Before he can, however, Georgina visits Dan and tells him that she's pregnant with his child.

Season 4

It is revealed Georgina had a son, Milo, on July 7, 2010, but it is unknown if Dan is the father, because they never did a DNA test. It is later revealed to be another one of her schemes when she abruptly leaves New York, leaving Dan alone with Milo. She left a note saying that she went to the "spa". Georgina returns from the "spa" (she was in fact in St. Barts) to tell Dan about Serge, Milo's real father, and to say that she and Milo are going to live with Georgina's parents. Dan is sad to see Milo go. He tries to embark on a relationship with Serena, who is still torn over him and Nate. Blair and Dan team up to find Juliet in Connecticut. They do find her with Serena, but get a shock when Serena tells them that Lily was the one who put Ben in jail instead of herself. It was revealed that Blair and Dan went to see a couple of movies together, though the both say that they are not friends. Blair was fired from her internship at W Magazine, but since Dan connived to get her fired, he confessed and convinced Epperly to re-hire Blair. Hereafter, Blair got better position as a team leader, since her boss decided to retire. On Valentine's Day, Blair found out that Chuck had real romantic feelings for Raina Thorpe. Dan stalked Blair to try to convince her to publish his short story, and the two of them made the discovery together (Chucks real feelings for Raina) while hidden behind a curtain. They went their separate ways, but spent the rest of the evening talking together on their cell phones while watching Rosemary's Baby on their laptops. Afterwards, both got a hidden closed relationship and denied the friendship to everybody. Feeling something beyond that happened, they tried to overcome the all confusions and denials by only one kiss. Later, Dan admits to Eric and to Charlie that he has romantic feelings for Blair.

In the finale, it was revealed that Dan had been writing a story on and off again for the past five years.

References