Gossip Girl’s Not-So-Lonely Boy: A Dan Humphrey Dating History
(Also, Dan and Serena have a half-sibling! Remember Scott?) When Claire Willett made her (impressively well thought-out) Twitter thread. Daniel Randolph "Dan" Humphrey is a fictional character in the best selling Gossip Girl (novel . 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. In conclusion, Dan and Serena are the worst. thrown into the mix to create conflict in relationships we actually liked, and it was a relief when.
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: 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.
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.Dan Serena DERENA love story (Gossip Girl)
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.
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. This reveals his true feelings for Serena as he shows obvious anger towards Serena's "cheating. 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 hypocrisyDan 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. After a long talk and a bit of arguingthey 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 YaleDan's recommendation for Yale admission goes awry as his only recommendation came from J. 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. 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. 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.
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. 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. 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.
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.
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. 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. 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 CNNthat 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 finaleDan 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 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.
It is later revealed to be another one of her schemes when she abruptly leaves New York, leaving Dan alone with Milo. Blair and Chuck struggle with admitting their feelings for one another. Chuck and Blair are in an official relationship, but wonder whether it will work out without games.
Serena defers Brown and tries to find ways to make herself useful in Manhattan. Chuck purchases The Empire Hotel. Blair and Serena try to figure out their friendship as they grow and mature.
Nate and Serena and Dan and Vanessa begin dating but find that dating your best friend isn't without its complications. Meanwhile, Eleanor and Cyrus move to Paris full time. Serena's father William arrives back in town and reveals a secret about Lily.
Dan–Serena relationship | Gossip Girl Wiki | FANDOM powered by Wikia
Blair and Chuck separate, after he commits two unforgivable acts. Blair and Serena begin at Columbia but face challenges at their new school.
After keeping it secret for so long, Lily serves a house arrest sentence for forging Serena's signature on a legal document. Blair is pregnant with Louis' baby but ultimately loses it. The two get married, then divorced. Dan and Blair begin a romantic relationship. Charlie's real identity is revealed to everyone, as is who put her up to it and why.
Gossip Girl's identity is revealed: Blair and Serena seek to deal with the biggest roadblock in their friendship ever.