Dan Humphrey

Dan Humphrey
Gossip Girl character
Penn Badgley as Daniel Humphrey
First appearance	Novel: Gossip Girl Television: "Pilot" (episode 1.01)
Last appearance	Novel: I Will Always Love You Television: "New York, I Love You XOXO" (episode 6.10)
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)	Dan Television: Cabbage Patch (by Blair) Humphrey (by Blair) Lonely Boy (by Gossip Girl) Brooklyn (by Chuck)
Aliases	D, Lonely Boy
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 NYU) Former W Magazine intern
Family	Rufus Humphrey (father) Jennifer "Jenny" Humphrey (younger sister) Novels: Jeanette Humphrey (mother; estranged) Television: Alison Humphrey (mother; estranged) Lillian "Lily" van der Woodsen (former stepmother) Scott Rosson (paternal half-brother)
Spouse(s)	Television: Serena van der Woodsen (wife; flash-forward)

Daniel Randolph "Dan" Humphrey is a fictional character in the best selling Gossip Girl series of novels. He is one of the central male characters in the television adaptation of the same name, where he is portrayed by Penn Badgley. Dan Humphrey is the son of Rufus Humphrey and has a younger sister, Jenny, while his mother remains absent for the majority of the series. Dan and his family live in Brooklyn, New York, the alternative of the old-moneyed and conservative Upper East Side. He attends St. Jude's Preparatory School for Boys on the West Side as a scholarship student. His life changed dramatically when his father, Rufus Humphrey, married the wealthy Lily van der Woodsen, moving the family to the Upper East Side.

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

Daniel Humphrey lives with his father Rufus, and sister Jenny in Upper West Side, New York. He is tall, pale, quite neurotic, quite "intense" and 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 School for Boys, on the Upper East Side, 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, Greg, in the Strand by making literary salons with him, which were, in actuality, giant orgies. He breaks up with Greg, who becomes Chuck's boyfriend instead. Dan realizes that he truly loved Vanessa. He went to The Evergreen State College for bachelor studies.

Television 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 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. During the beginning of the show Dan has had somewhat of a disgust towards Serena's childhood best friend Blair Waldorf, however as the seasons progressed he develops a close friendship with her.

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 hooking up at a party 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 on the Upper East Side with the intent on making Serena's life hell, she gets to know Dan behind Serena's back. Pretending to be "Sarah" and accidentally-on-purpose letting her dog run off its leash in the park, Georgina gets an excuse to talk to Dan. It is later seen that Dan and Vanessa have taken "Sarah" under their wing as they believe she is a new girl to the Upper East Side who doesn't know her way around.

Eventually, Dan breaks up with Serena, because he believes 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 Christian boot camp. 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) 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 have some fun. 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 of 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. Even though Rachel is reinstated, she and Dan have sex again before the school play. Dan then discovers she has used things he told her to humiliate Serena and Blair on Gossip Girl, as well as blocking Blair's application to Yale. He tells the girls what has been going on and Rachel leaves the school.

Dan is accepted at Yale but denied financial aid. He discovers Rufus has invested his college fund with Serena's new boyfriend Gabriel Edwards, who was working with con artist Poppy Lifton. Not trusting Serena, Blair and Chuck to get the money back, Dan goes to Lily for help, resulting in her getting Serena arrested to stop her exposing Poppy. With money from CeCe and a dress from Jenny, Dan manages to bail Serena out of jail and take her to the prom. On graduation day, Dan refuses to take part in Serena's plan to expose Gossip Girl, which results in everyone's secrets, including Dan being arrested, becoming common knowledge. Dan gets a call from Georgina saying the money Poppy took is back in his account and tells her he's going to New York University.

Season 3

Dan joins Blair, Vanessa and Georgina at New York University and instantly fits in among its 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 Hollywood film star who attended NYU to experience life as 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 other's 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 the Tisch School of the Arts writing program at NYU, 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

"You've always wanted in...maybe more than Jenny." —Vanessa reveals Dan's secret desire to be a part of the Upper East Side

It is revealed Georgina gave birth to a son, Milo, on July 7, 2010, though it is unknown whether 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. Barths) 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 scathing novel based on his life for the past five years. While looking for Charlie at the loft, Vanessa reads his novel and hints at the possibility that he possesses unrequited feelings for Blair all the while realizing that Dan always wanted to be a part of the Upper East side. Vanessa encourages him to publish the novel following in a harsh exchange of words during a phone call and resulting in Dan lashing out at Vanessa while she takes matters into her own hands leaves the Humphrey apartment with his novel. Later scenes during the finale show Vanessa offering Dan's novel to a publishing company.

Reaction to triangle

"Chuck and Blair are always going to be connected in their way, and Dan and Serena are always going to be connected in their way. But that doesn’t mean that there won’t be new roads to go down that might be different than what we initially anticipated." —Joshua Safran, producer

Amidst the fourth season, the romance between Dan and Blair became a polarizing topic among viewers which also drew significant media interest. Jarett Wieselman of the New York Post applauded the development, feeling that Blair had "more chemistry" with Dan than with Chuck. New York magazine's Chris Rovzar called Blair and Dan's story line "believable", citing their common ground in education and taste. Rovzar further stated, "Since they live in a world where both only seem to have half a dozen real friends (if that), is it so crazy they'd end up together?" Dawn Fallik of The Wall Street Journal was less positive, asserting that "both characters have been so Blandified that there’s no fun left in the show." A writer for E! Online's Team WWK labeled the Dan/Blair relationship "nomance nonsense".

With regard to Chuck and Blair, Meester stated, "I can really relate to it—not necessarily because it's this dramatic, tumultuous relationship, but because the way they love each other is very real, and not for the sake of being dramatic. It's actual love. There's nobody for each other but them." Meester also expressed fondness for Dan and Blair, however, stating, "I think they're good for each other in a lot of ways, in a way that Chuck and Blair aren't."

Producers initially noticed chemistry between Blair and Dan in the Season 1 episode "Bad News Blair". According to producer Joshua Safran, the creators planned to revisit their relationship once the timing was right. Safran also stated that the outcome wasn't necessarily decided ahead of time. "One thing we are very conscious of—and I know some fans get upset about this—is we really try to treat the characters as living, breathing, well-rounded individuals. And we're often surprised by where their journeys take them; they open new doors for us all the time."

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, 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 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, 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 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.

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 bulimic ways. He voices out his concern and Blair leaves the washroom stall, stating that she was not bulimic, 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 paparazzi tail them continuously after Charlie sends Gossip Girl a blast, informing her on Chuck and Blair's whereabouts.

The accident causes Serena, who is alongside Nate and Dan, to be more furious at Gossip Girl than ever before, and blames her entirely for the accident caused. Dan monotonously 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.

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.

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.

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.

However, unknown to Blair, Dan was the one who wrote the vows, after Louis asked him to. On her wedding day, Blair and Chuck 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.

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 altar, 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 she always will, just before Louis and Blair take their first dance as a married couple. 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.

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.

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 Blair and stunned and angered Serena alone together. Blair continues to deny having any feelings for Dan during and after the party to both Dan and Serena.

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.

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.

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 that 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.

In the episode's last scene, 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.

The new couple make a slow and rocky debut on the Upper East side and are faced with numerous challenges including their relations in the bedroom, Blair's lingering feelings for Chuck, and Serena's distaste for their relationship. 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 finale, 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

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 and Serena throw their first Thanksgiving as a couple together, 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 into the Upper East Side drama 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 he had for Serena. 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 in the Upper East Side with Dan.

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