Dan Humphrey

Daniel Randolph "Dan" Humphrey is a main character in the Gossip Girl television series and the the novels. He is portrayed by actor Penn Badgley.

Dan has an on-again, off-again relationship with Serena van der Woodsen throughout the series, the two have the longest running relationship on the show and serve as each others primary love interest. Dan and Serena finally get married in the finale.

Dan is good friends with Nate Archibald and Blair Waldorf, he is also a frenemy to Georgina Sparks. In the sixth season, Dan reveals himself to be the anonymous blogger known as Gossip Girl.

He, Blair and Serena are the only characters that appear in every episode of the TV series.

Summary
Dan "Lonely Boy" Humphrey is the son of rock musician Rufus Humphrey and artist Alison Humphrey, and is the older sibling of Jenny Humphrey. Dan is a poet and used to attend the St. Jude’s School for Boys with enemy Chuck Bass and previous rival for his love interest and now best friend Nate Archibald. Although accepted to Yale, he now attends NYU. He used to long for Serena van der Woodsen since a party when they were in ninth grade, and she was the only person who talked to him. He used to despise Serena’s best friend, Blair Waldorf; but became best friends with her and has since dated.

Dan is clever, witty and patient; he works hard for what he wants and normally achieves his goals. Although unexperienced with plotting and manipulation, he demonstrates promise when scheming with Blair. Dan reveals at the end of the series that he was Gossip Girl from the beginning for a way for him to win Serena by writing himself into the Upper East Side, a task he succeeded in by the end of the series. In the finale, Dan and Serena get married, surrounded by friends and family.

Novels
Dan 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 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, as a scholarship student. At the end of the series, he matriculates to Evergreen State Collegein 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 and chain smokes cigarettes. He over analyzes 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.

Television series
Son of rocker Rufus and artist Alison, Dan is the oldest of their two children. He had a crush on Serena van der Woodsen from the age of 15 and was one of the kindest people to her when she returned from boarding school. He is attractive but he often felt beneath his rich classmates.

In Season 1, he was extremely protective of his younger sister Jenny, he was especially concerned when she decided to become a part of Serena's best friend Blair's group which involved her spending a lot of her time pleasing the Queen Bee.

His most noted relationship is often seen as his on-again, off-again relationship with Serena. They remained close and Dan was always at her side when she needed help, and said that he would always be there for Serena. He is friends with Nate Archibald the rich son of Howard and Ann Archibald. He is also now best friends with Blair Waldorf and has since dated.

In the final season, Dan becomes a successful author and makes a transition into films. He also moves out of Brooklyn and into the UES. Dan and Serena decide to rekindle their love for good in Season 6 and get married five years later, surrounded by friends and family.

Season 1
Dan is introduced as a resident of Brooklyn, a poet who aspires to attend Dartmouth College. He attends St. Jude's School for Boys, but as he is financially lower-class in comparison to his rich Manhattan classmates, he is something of an outsider and tends to be ignored by everyone. He lives with his younger sister Jenny and father Rufus, who is separated from his mother. He has had a crush on the Upper East Side's former It Girl Serena van der Woodsen for several years, and is one of the first people to personally see her back in New York. He walked into her at a bar, causing her to drop her purse and spill things. In her haste to leave after being assaulted by Chuck Bass, Serena leaves her cellphone behind. The following morning, Dan goes to the hotel where Serena is living to return her cellphone. To get out of the Kiss on the Lips party being held by Blair Waldorf, Serena goes out on a date with Dan. They first went to Rufus's concert, but the date was interrupted when Jenny sent multiple text messages to Dan asking for help. When Dan and Serena went to investigate, they found a protesting Jenny being attacked by Chuck. Consequently, Dan punches Chuck, who shortly afterwords tells Serena that her life is over.

After an awkward end to the date, Serena and Dan go out again, but have a fight when he finds out about Serena's one night stand with Nate Archibald, Blair's boyfriend. This was the reason she left boarding school, and Dan and Serena make up. Vanessa Abrams, Dan's best friend, suddenly returns. Jealous of Serena and still in love with Dan, Vanessa tries to show him that she is a better choice than Serena and her glitzy lifestyle. Dan is oblivious, but Serena notices and is made uncomfortable. She also becomes worried when she finds out about Dan's mother's return from Vanessa instead of Dan himself. Dan's choice is made clear when he and Serena sleep together for the first time at Christmas.

A few weeks later, Dan goes to see what Jenny is doing. She has her laptop open to the Gossip Girl site, and hastily closes it before Dan can see. Rufus also walks over, suspicious of Jenny's odd behavior, and she is forced to show them what she was looking at: pictures of Serena buying a pregnancy test. Rufus is extremely upset over the possibility of Dan being a teenage father. Realizing the child could be his, Dan confronts confronts Serena. She lets him know that she was actually buying the test for Blair, who turns out not to be pregnant. Dan calms down but feels awkward, as he blurted out that he loved Serena and she only responds with 'okay'. It's not the response he was looking for and causes him to have some doubts. Later, Serena asks why he loves her, and after telling her, she says she loves him too.

Georgina Sparks returns to the Upper East Side after rehab in Switzerland. She used to be a close friend of Serena, and the two of them got into a lot of trouble together - partying, drinking and doing drugs. Georgina is confused and annoyed to see Serena has changed her ways and doesn't want anything to do with her, but spikes her drink when the two of them go out to talk. This leads to Serena partying all night, then waking up remembering nothing, and missing her SATs which she later retook. All of this she hid from Dan, as Georgina was blackmailing her with a dark secret that she and Serena shared. Georgina later decides to get revenge by getting close to Dan, pretending to be 'Sarah', a new girl in town who doesn't know her way around. Clueless, Vanessa and Dan become best friends with 'Sarah'. Serena goes into a downward spiral, and lies to Dan, telling him that she slept with someone else. He breaks up with her and leaves, saying "I'm done."

Serena absolves the guilt over her secret - a year ago, she suggested she and a drug addict called Pete do some coke. This was to put off sleeping with him. However, when Pete followed Serena's instructions and did a line, he overdosed and died. Even though Serena called 911, she has held herself responsible ever since. When Pete's parents told her they didn't blame her for what happened, Serena goes to a concert featuring Rufus's band with the intention of telling Dan everything and mending their relationship. She just misses seeing him, and when Georgina (still pretending to be Sarah) finds out that her intentions of blackmail are now invalid, she pulls Dan into the street and they kiss, with Dan completely unaware that Serena is at the concert. The next day, it is revealed that although Georgina spent the night with him, they didn't sleep together, but they may have well as. He is recruited by Blair Waldorf to help bring down Georgina, which he does by bringing Georgina to a park where Blair takes her down. He attends Lily and Bart's wedding as Serena's date where he breaks up with Serena for not being honest with him. The end of season shows Dan and Vanessa (who also just broke up with Nate) talking about what happened, possibly alluding to a Dan/Vanessa relationship.

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 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 in 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 of 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 on 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 repairs 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 and with Dan becoming popular at NYU, leaving Blair ostracized.

Dan and Georgina's relationship is short-lived in the episode The Lost Boy. Georgina has Blair in 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 that 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 lovechild 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 Ronson is his half-brother, the lovechild 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 lovechild. Dan arrives with the rest of the family and confirms Georgina's statement. Dan and Blair find Georgina eating the wedding cake and Blair leaving. 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 embarks on a new relationship with Vanessa, confessing his love for her during Bart Bass' death anniversary and Vanessa turning 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 in a beach party when Dan arrives with a fresh date and Vanessa getting 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 at Dan appreciating what she did for her date, 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
Georgina had her son, Milo, on July 7, 2010. She later goes on to say that she did a paternity test in order to prove that Dan was the father. However, it is later revealed to be another one of her ploys for revenge when she leaves Dan alone with Milo, never to be heard from or seen again. She left a note saying that she went to the "spa". In the “Double Identity” episode, Rufus finds Milo’s ID bracelet, which says that Milo has a different blood type than Dan. Dan and Vanessa slept together, after Nate told Vanessa (with Juliet’s help) that Dan still has feelings for her. In the end of the episode, Dan admits to Vanessa that he still has feeling for her, since Gossip Girl said Serena was back in town. In the "The Undergraduates" episode, Georgina comes back from the "spa" (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 leave. Vanessa move in with Dan. In the "Touch of Eva", Blair, Serena and Dan found out that Eva was a prostitute. Dan tells Nate about Eva. Nate then tells Chuck about Eva. Chuck confronts Eva but forgives her later on. Frustrated, Blair look at other means to get rid of Eva, which she succeeded in. Eva leaves and Chuck is torn. Chuck confronts Blair and declares war. Dan found out he still had feelings for Serena, but eventually went back to Vanessa. Serena is seen lying on her bed alone, depressed.

While Serena's in rehab, Dan goes to visit her and she tells him that she picked him and not Nate and at the end of Gaslit they kiss and agree that they have just one more chance to be together. They have already been together three times and they need to be sure the 4th time is forever before getting together again.

Blair finds out Juliet was behind Serena's overdose and enlists Dan's help in clearing Serena's name. The two embark on a road trip to Connecticut to track down Juliet. After discovering that Juliet's brother, Ben, was a teacher at Serena's former boarding school, the twosome return to Manhattan armed with this new information, only to discover that Serena has already taken matters into her own hands.

Over winter break, Dan and Blair find themselves alone together in New York, and end up attending a screening of "Nanette" at Film Forum together. Though they were intent on this secret rendezvous being a one-time occurrence, the two soon find themselves repeatedly making plans to spend time together.

Dan and Blair's budding friendship is challenged when they discover that they're now rival interns at W magazine. Blair admits to Serena that Dan is her only true competition in the internship, as he has proven himself her equal. Blair considers sabotaging Dan, but decides against it. However, Dan, assuming Blair would stick to the pact, sabotages her. Once Blair finds out, she attacks Dan at the party, and they both end up getting fired. Later, when Dan finds out how hard Blair worked to get the internship, he tells their supervisor that he was to blame, and gets Blair her dream job back.

Dan asks Blair for help in getting an article he's written to editors at other Conde Nast publications, which Blair refuses to do. While talking to Eric, Dan admits he wants to spend Valentine's Day with Blair, but says it's just because he needs her help. Later, at a Valentine's Day party, Dan follows Blair while she is looking for Chuck. When Chuck walks in with Raina Thorpe, Dan and Blair hide, and Blair learns that Chuck has real feelings for Raina. Dan sits with Blair and takes her hand in his, trying to comfort Blair. She later calls him and says that she enjoyed his article and gave to an editor at another magazine. The two spend the rest of Valentine's Day on the phone together, while watching Rosemary's Baby in their own beds.

When Blair begins to overextend herself, Dan offers to help her as a friend, but only if she admits that she needs him. She initially refuses, but eventually gives in. Later that night, she comes to the loft and tells him that she was "fired/quit" from the magazine because she was "imploding". Dan once again comforts her by asking her to stay. They end up falling asleep together on the couch while watching a movie.

Dan reluctantly goes along with Blair's plan to keep their newfound friendship a secret. However, Dorota becomes suspicious of Blair being particularly cheerful (as a result of spending time with Dan), and when she finds a magazine of Dan's in her bedroom, she accuses them of having an affair. Then, when Dan receives some surprising advice from his dad about his secret relationship with Blair, he begins to wonder if there could be something more going on between him and Blair. In order to convince people that they're not falling for each other, Dan and Blair agree to announce their friendship during a party. But they don't get a chance when their friends are distracted by Lily turning herself into the police, and they reluctantly decide to end their friendship. However, Dan arrives at Blair's home later that night and suggests that they should confront the possibility that they actually are falling for each other with a kiss. After an awkward hesitation, Blair finally has to pull Dan to her and kisses him.

While the kiss made Dan realize he has for feelings for Blair, which he eagerly wants to discuss with her, but the kiss only made Blair realize she should be with Chuck only. Blair spends the week following the kiss in her room (afraid to face how the kiss made her feel). While working at a photoshoot for prominent families, Blair tells her former supervisor at W, Epperly, that she recently shared a "life changing" kiss with someone, who immediately tells Chuck. Chuck then goes over to the loft to see if Dan might know who Blair kissed. Dan is clearly excited when he hears the kiss was "life changing" for Blair. By the end of the conversation, Chuck realizes it was Dan Blair kissed. He gets Dan invited to the photoshoot to be humiliate him in front of Blair. When Dan and Blair confront Chuck about it, he says he knows that they kissed. Blair claims that it made her realize she should be with Chuck (which clearly upsets Dan), but Chuck's actions make Blair realize that they should wait to be together.

Dan is hired to cover the Prince Louis' visit to Manhattan. But, when he discovers that Louis is with Blair, he backs out of the job. In order to help the pair to maintain their secrecy, Dan and Blair stage a kiss at the Pink Party to be witnessed by an adviser of Louis', in order to convince him they're dating. Meanwhile, Serena has become aware of Dan and Blair's first kiss, and has had her cousin Charlie follow Dan. Charlie follows Dan and Blair at the party, records them making out, and sends it to Gossip Girl. Serena confronts Dan and Blair about their relationship, and they say they've only been hiding that they're friends. When asked about their first kiss, Dan and Blair tells Serena it was just an experiment. When Serena is still upset with them, Dan walks out. Blair then argues with Serena, telling her that she and Dan have a genuine connection that has nothing to do with Serena. Later that night, Charlie comes to the loft to apologize to Dan for exposing him and Blair. She says she could tell by the kiss that Dan really likes Blair. Dan agrees with her and says he never expected he'd have feelings for her.

Season 5
Season 5 of Gossip Girl begins 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 magazine 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, and just as they were about to make a move, Louis comes 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. And at the end of the episode it's been 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 bullimic. 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, in order 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, but she tells him that it was all Chuck's doing, driving him to go searching for Chuck. To his horror, he finds Chuck getting beatened 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 dillemma.

Meanwhile, at the feast, Blair begins to feel sick and searches for an excuse to run to the bathroom without arising suspicion. She begins to silently pray to God for a way out, and once she finishes, she sees Dan at the front of the door. Blair rushes to his side and drags him to the toilet and orders him to guard the door. Dan announces that Chuck is getting himself into trouble again, but Blair brushes it off, stating that he's merely doing it to get her attention.

Once Dan hears Blair throw up, he begins to get worried and, like Beatrice, assumes that she has gone back to her previous bullimic ways. He voices out his concern and Blair leaves the washroom stall, stating that she was not bullimic, but instead pregnant. However, Beatrice walks into the bathroom just as Blair reveals her pregnancy to Dan. The both of them are shocked, but agree to keep it a secret.

Afterwards, Blair arrives at Dan's loft once again, revealing to him that she is uncertain who the father of her unborn child is. He encourages her to take a test, but she refuses, stating that she'll lose everything if Chuck is the actual father. Dan responds that she will still have him, causing Blair to cry and rest her head on Dan's shoulder. He then kisses her forehead.

However, Blair, being her usual self, still tries to avoid taking the test, but after much persuasion from Dan, she eventually does, and announces that the father is Louis. She then tells Louis that she's pregnant, much to his elation. Soon afterwards, Serena, Nate, Chuck, Louis's mother, Eleanor and Cyrus all know about Blair's pregnancy, and she decides not to keep anymore secrets regarding her unborn child.

Dan decides that it is time for him to tell Blair about his feelings for her, engaged or not, when she comes and visits him at his loft, feeling heavy-hearted and dejected. She tells him that she wishes to be happy again, but has forgotten how to be.

After a very emotional phone call with Chuck, Blair enters Dan's living room heartbroken, looking devastated and emotionally drained. This drives Dan to attempt and bring Chuck and Blair together again, determined to bring joy back into Blair's life. He decides to keep his feelings for Blair quiet and bottled up, only letting Serena know how he feels about her.

Dan leads both Chuck and Blair individually into an enclosed candlelight room. Once they both come face-to-face, Dan closes the door and shows himself out, leaving them both alone. Then, he engages in a discussion with Serena, telling her that all he wants is for Blair to be happy. Serena to tells him that he's one of the good guys, due to his selflessness regarding Blair's happiness.

While Blair and Chuck are whisking away in a limo, planning on running away together and raising Blair's unborn baby as Chuck's child, they both end up in a serious, life-threatening car accident when poparazzi tail them continuously after Ivy sends Gossip Girl a blast, informing her on Chuck and Blair's wherabouts.

The accident causes Serena, who is alongside Nate and Dan, to be more furious at Gossip Girl then ever before, and blames her entirely for the accident caused. Dan montonously states that she didn't jump on one of the motorcycles and chase Chuck and Blair down the road, but Serena angrily responds that the accident is merely the result of all the amount of damage that Gossip Girl has caused throughout the years. Nate agrees, and he Serena begin planning on taking Gossip Girl down for good, to avenge Chuck and Blair, as Dan anxiously waits for news on Blair.

In the next episode, Blair learns that she lost the baby in the accident, much to her depression and despair, and she immediately bursts into tears when the news reaches her. She becomes even more terrified when Serena tells her that Chuck is in serious danger, due to losing a large amount of blood. This drives her to make a secret deal with God, promising him that if he saves Chuck's life, she would marry Louis and not go back to being with Chuck. Once she makes the promise, the nurse informs her that Chuck is asking for her. She decides that this means that God has honored their promise, and chooses to further her relationship with Louis, deciding against pursuing her relationship with Chuck.

She informs Dan about her deal and tells him to keep it a secret, to which he agrees. Soon, only Dan and Serena know about Blair's promise. She begins avoiding Chuck and Louis, who collaborate to find out what was going on with Blair, and find pictures of Dan and Blair together in New York, learning that the only man she's not avoiding is Dan.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">When she tells him that she needs him, and he responds that he has her, once again confirming that he will be there for her during the hard times.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">When Dan walks in on Blair in her wedding dress, he tells her that she looks perfect, making her cry. She says that she can no longer get married in the dress, as now all she sees is everything she's lost. Dan comforts her and tells her that she should change her mind about marrying Louis, but she insists on pursuing the wedding, stating she's committed to him.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">They both falsely assume that she's having an affair with Dan, to which she immediately denies. Soon later, she finds Louis's wedding vows, and is pleasantly stunned with how accurately he describes her and how much love the vows display. She tells Serena that she feels as if Louis had "peered into her soul", and now is happy with the decision she had made, believing that Louis is the one for her.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">However, unknown to Blair, Dan was the one who wrote the vows, after Louis asked him to. During the wedding day, Chuck and Blair confront each other once again, and Blair declares that she does indeed love him, but cannot be with him. She leaves the room to attend the ceremony, leaving Chuck alone in the room.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">Cyrus and Harold both give Blair away, and Dan and Serena walk down the aisle together. However, it appears that someone taped Chuck and Blair's moment, when Blair was professing her love for Chuck to him. It sends Blair running down the aisle and causes her to blame Chuck, assuming he was the one who sent the blast to Gossip Girl. Soon, she returns to the alter, and she and Louis continue the wedding. After Louis and Blair say their vows and take each other as man and wife, Serena tells Dan that she loves him, that she always had and always will. As Blair tells Louis that she's very thankful for giving her a princess title and especially grateful that he gave her another chance, he coldly responds that their wedding was all for show and there is nothing but a contract between them. He tells her that when they're alone, they'll become like strangers to each other.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">After the wedding, Dan is certain he has lost Blair to Louis but soon finds out it is a sham wedding when Blair asks him for help to get out of the country and file for a divorce. Taking her to the airport he realizes just how much she needs to get out of this situation and lies to Serena about her whereabouts, this leaves him with a problem when he is discovered with Blair later on.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">Soon afterwards, Blair arrives from her honeymoon to Manhattan on Valentine's Day, she tries to set Dan and Serena up once again. However, when Blair notices the lack of interest Dan has in pursuing his old relationship with Serena. She tells him that she attempted to get Dan and Serena back together because she wants Dan to be happy. Blair asks him what it is that would make him happy, and he responds by kissing her, leaving Blair stunned. She, however, does not stop him and instead slowly begins to reciprocate to the kiss. Unfortunately, Serena, alongside Georgina, accidentally intrudes on Dan and Blair. Georgina manages to snap a picture of Dan and Blair's kiss and soon runs away from the scene, driving Dan to chase after her, leaving a stunned Blair and an angered Serena alone together. Blair continues to deny having any feelings for Dan during and after the party to both Dan and Serena.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">With Serena and Blair's friendship on shaky grounds Dorota decides to lock them in the dining room up for their own good. Blair decides to prove to Serena by spending a whole day with Dan that her feelings are platonic. Unfortunately, she reciprocates another kiss from Dan while Serena accidentally intrudes on them. Serena dictates that Blair is always in denial when it comes to matters of the heart. During a re-enactment of a scene from the Inside novel, Blair realizes that Dan loves her for her and has so for some time. Putting aside her insecurities she admits to both Serena and Dan that she too has feelings for Dan. Serena then gives Blair her blessing, stating that she does not want to be an obstacle in Dan and Blair's relationship. Soon afterwards, Blair pecks a kiss from Dan and heads off to support Serena with her last moments with CeCe.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">In "The Princess Dowry" Dan walks in on Blair discussing what could be a potential way out of her prenup on the phone with Cyrus and another lawyer from his firm. Blair shares the details and after saying that she "wouldn't have to wait a year for ... anything" she and Dan exchange smiles.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">At Cece's wake Chuck outs Dan via Gossip Girl as the sender of the video that was fatal to Blair's marriage. At first, she thinks that it's just a game Chuck is playing and she is unwilling to participate, however, when she sees the guilty looks on Dan's face she realizes that it's the truth. She is mad at him, but forgives him after he tells her that his only reason for sending the video was that he couldn't stand to see Blair so unhappy. Meanwhile, Blair makes a deal with Estee to help her get out of hr marriage dowry if there will be no more public mention of it in the media, including Gossip Girl. However, at this time Georgina, who has stolen Dan's phone, teams up with Chuck and sends Gossip Girl a message from Dan's phone uploading the photo of the Valentine's Day kiss, thus ruining Blair's chances of not having to pay the dowry. Dorota shows Blair the blast and she confronts Dan who is confronting Georgina. The latter admits to having been Gossip Girl and it turns out that the deal with Estee was also one of her schemes. Dan goes to confront Chuck, who, after finding out that the blast will bankrupt Blair's family, is regretful, however, he revels thats he has outed Dan for the bad guy he has been and he question whether their friendship was just an act. Blair walks over to them and Chuck tells Dan to be honest and confess that he has been trying to keep him and Blair apart, which Dan does. He apologizes to Blair and leaves. Chuck says that wants Blair and him to try again because all the obstacles that were in their relationship's way are seemingly gone, but Blair tells him that although she loves him, she is not 'in love' with him anymore. Later Georgina visits Blair and promises to get her rid of her dowry in exchange for Blair's support. Blair agrees to this.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">In last scene of the episode Blair goes to Brooklyn. Dan isn't expecting her, as he is assuming she got back together with Chuck. Blair tells him that she isn't there to tell him off and she isn't with Chuck. Dan cracks a joke that clearly expresses his disbelief and surprise at Blair choosing him over the 'love of her life' Chuck. She tells him that she told Chuck that he doesn't have her heart anymore as it now belongs to someone else. They kiss and rest their foreheads against each other's. Blair calls him by his first name which amuses Dan and he asks her to "say it again" and they start kissing passionately. Their relationship keeps on growing and Dan acts like a perfect boyfriend making Blair feel happy, safe and strong around him.

<p style="margin-top:0.4em;margin-bottom:0.5em;line-height:19px;font-family:sans-serif;">However, in the finale when Gossip Girl intentionally exposes Blair's secrets on Gossip Girl, Dan comes to terms with Blair's feelings for Chuck, as well as Serena's attempts to sabotage their relationship. In the final scene, Dan, having been left by Blair for Chuck, teams up with Georgina in order to write his follow up to "Inside". This time, however, he pledges to write the novel "he should have written from the beginning". Georgina, with her own score to settle with the Upper East side, is more than happy to help.

Season 6
Dan tells Serena that the reason he didn't give her an answer to the "I love you" was due to the fact that it was easier to focus on his anger at Blair, then to face the possibility of getting what he always wanted in the fear of losing it again. Dan and Serena throw their first Thanksgiving as a couple, where Serena affirms her love for Dan

by rejecting both Steven and Blair by saying that Dan is her soul-mate and the only love of her life. 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 in to the Upper east side (UES) by using a blog to create a legend, the blog came to be known as Gossip Girl. Dan then revealed his secret to all by giving Nate his final chapter to publish in the struggling Spectator. Revealing to all that the only purpose of Gossip Girl was the love Dan had for Serena. Serena was joyed at the revelation, stating that Dan through Gossip Girl, wrote her and everyone else a seven year love letter and made her realize that she belongs in the UES with Dan.

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

Style and appearance
Dan is often seen in casual clothes, in Season 1 he expressed his dislike for tuxes and suits. He often wears jeans and a t-shirt, a fact that Jenny tells Serena when asked what to wear for their first date. Dan has been known to dress up when needed though, such as when he goes to parties or important social events. As the Seasons progress and he becomes a part of the van der Woodsen family Dan starts to wear more designer clothes; he has a designer wallet which Vanessa notices.

Personality
Dan is very knowledgeable and has a huge sense of justice (a good guy type). He strongly cares about the people he loves and is very protective, especially when it comes to Jenny and Serena. Dan has had a tendency to be judgmental and self-righteous in the past. He is also a hopeless romantic.



Relationship with Serena
Dan's defining relation on the show is with Serena van der Woodsen, he met her at a party a year before the pilot episode and immediately fell for her. The two start dating in the first episode of the show and continue their on-off relationship all throughout the series, leading to their wedding in the series finale

Novel Series

 * Rufus Humphrey (father)


 * Jeanette Humphrey (mother)


 * Jenny Humphrey (younger sister)

Television series

 * Serena van der Woodsen (Wife)


 * Rufus Humphrey (father)


 * Alison Humphrey (mother)


 * Jenny Humphrey (younger sister)


 * Scott Ronson (paternal half-brother)


 * Lily van der Woodsen (Mother-in-law) (used to be step-mother via Rufus)


 * William van der Woodsen (Father-in-law)


 * Eric van der Woodsen (Brother-in-law)


 * Lola Rhodes (Half-sister-in-law)


 * Chuck Bass (Adoptive Brother-in-law)

Novels

 * Serena van der Woodsen


 * Vanessa Abrams

Television series

 * Serena van der Woodsen (Wife)


 * Blair Waldorf (ex-girlfriend)


 * Olivia Burke (ex-girlfriend)


 * Rachel Carr (fling)


 * Vanessa Abrams (ex-girlfriend)


 * Ivy Dickens (kissed)


 * Georgina Sparks (fling)

Books
Dan's first published book was 'Inside', but Vanessa had it published anonymously with Dan taking credit later.

His second book, 'Monarch of Manhattan' is first sabotaged by Chuck, who later fixes his wrongdoing. It is unknown whether this book is ever published.

His next book, the sequel to 'Inside', is called 'Inside Out' and is published in chapters. The first and last chapter are published in Nate Archibald's paper, The Spectator, whereas all the others are published in Vanity Fair. Each of the chapter's are about his friends on the UES, and the final one is about him and his revelation as to who gossip girl is.

Quotes
Dan (to Serena): I’m sorry that I didn’t say anything when you told me you loved me. Maybe it was easier to focus on my anger at Blair than face the possibility of what I always wanted and…and losing it again.

Dan: "You really wanna go out with some guy you don't know?"

Serena: "Well you can't be worse than the guys I do know."

Dan: Have you seen that movie, The Blair Witch Project?

Blair: What are you trying to imply, Humphrey?

Dan: Well, uh, she's best friends with this girl, Blair Waldorf, who is basically everything I hate about the Upper East Side distilled into one 95-pound, doe-eyed, bonmot-tossing, label-whoring package of girly evil.

Dan (to Chuck): Last time I checked I still owed you a black eye, so unless this is you coming to collect.

Dan (to Serena): The moment you walked away from me I knew I could never pull you out of your world into mine, but I couldn't give up.

Dan (to Serena): Serena I know that I have made mistakes, I have made massive heartbreaking mistakes, but I have never stopped loving you.

Dan (to Georgina): There is no winning without Serena.

Dan (to Blair): This whole time, I had more power than you.

Dan (to Serena): You have always been the one.

Dan (as Gossip Girl): Prohibition never stood a chance against exhibition. It's human nature to be free. And no matter how long you try to be good, you can't keep a bad girl down.

Photos
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