Dan serena relationship

Dan–Serena relationship | Gossip Girl Wiki | FANDOM powered by Wikia

dan serena relationship

Serena van der Woodsen and Dan Humphrey in the Gossip Girl TV Series. super cute Add an image. Summer skanks: When Dan and Serena are on a break after junior year, Lonely Boy Blair destroys their relationship, more or less for sport. Could a normal relationship withstand an attempt to sell the girlfriend for a Serena and Dan need to let the memory of their young love fade.

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. She left a note saying that she went to the "spa. 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. 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[ edit ] "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. Rovzar further stated, "Since they live in a world where both only seem to have half a dozen real friends if thatis it so crazy they'd end up together?

There's nobody for each other but them. Chuck or Dan, Westwick pointed to Badgley, saying "definitely him. 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.

And we're often surprised by where their journeys take them; they open new doors for us all the time. 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.

Dan Humphrey - Wikipedia

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.

dan serena relationship

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.

dan serena relationship

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 dayBlair and Chuck confront each other once again, and Blair declares that she does indeed love him, but cannot be with him.

Gossip Girl’s Not-So-Lonely Boy: A Dan Humphrey Dating History

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.

dan serena relationship

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 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 her 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 reveals 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. Season 6[ edit ] 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.

The relationship between Dan and Serenaalso known as Derena, is the friendship and romantic relationship between Dan Humphrey and Serena van der Woodsen.

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Contents [ show ] Overview Dan and Serena met at a party thrown by Blair Waldorf that Dan was accidentally invited to. They had a brief conversation that led to Dan having a huge crush on Serena. In Pilotthey accidentally run into each other at the The Palace Hotel and upon returning her cell phone; Serena asks Dan on a date.

They begin dating for the remainder of the first season before breaking up in Much 'I Do' About Nothing. They date briefly twice in the second season and then remain mostly off until season six. Novel Series In the Gossip Girl series of booksDan and Serena date very briefly but break up due to having nothing in common. Dan initially sees her return and upon learning that she's living at The Palace Hotel with her mother, Lily van der Woodsendecides to try and run into her there. While he's at the hotel, he accidentally collides with Serena; who is attempting to flee after rejecting Chuck Bass ' sexual advances.

After they both get up, he realizes she forgot her cell phone and attempts to return it the next day. They agree to meet for a date that night, where they would attend Dan's dad Rufus Humphrey 's concert. But before they can get to the show, they're called to Blair's party by Dan's sister Jenny Humphreywho is attempting to fight off Chuck from raping her.

They rescue Jenny and end the date. At the brunch, Blair informs Dan that Serena slept with her boyfriend, Nate Archibaldbefore she ran away to boarding school. Upset that Serena isn't as perfect as he always thought she was, Dan decides not to pursue a relationship with her anymore. In Bad News BlairDan and Serena attempt to go on another date but it gets sidetracked when Blair learns her mother passed her over in favor of Serena.

Dan takes the opportunity to talk to Blair and they agree to be civil to one another. Right after, Dan and Serena agree to go on another date alone. They eventually go on their date in Dare Devil and Dan plans a night with a rented driver and fancy dinner reservations wanting to impress Serena.

However, Serena is not impressed and admits she wishes they had done something more low-key. They abandon their dinner in favor of going to a bar and playing pool but their date is once again interrupted when they learn Serena's brother, Eric van der Woodsenhas escaped the rehab facility he is staying at after his suicide attempt.

They catch up to Eric, who is with Jenny, Blair, and Blair's friends, and escort him back to the facility. Afterwards, they share their first kiss and enter into a relationship. Add an image Dan's childhood friend Vanessa Abrams returns to town in The Handmaiden's Tale and Serena becomes jealous of their friendship, especially when she learns that they had feelings for each other at one point.

However, Dan assures her that he only has feelings for her and he's still learning how to be a good boyfriend. As a result, they have sex for the first time in Victor Victrola. During Thanksgiving in Blair Waldorf Must PieDan and Serena learn that their parents used to date very seriously when they were young. However, the revelation doesn't faze them and they continue their relationship. But when she learns that not only is Serena dating Dan but also not attending her Cotillion, she attempt to sway her by telling off Dan; who decides to go with Serena to the ball in retaliation.

After she hears this, CeCe offers to pay Rufus to make sure Dan does not go to the ball. When Dan discovers this, he tells Serena; who doesn't believe him. They decide not to go to the ball together, but Serena calls him to join her after she learns CeCe planned to set her up with Carter Baizen weeks before she even came to New York Hi, Society.

During Christmas, Serena is disheartened when she can't find the perfect gift for Dan. She later decides to work with Vanessa and Eric to set up a snow simulation in Rufus' art gallery, since she knows the only thing he really wants is a white Christmas. Wanting to support her, he blurts out that he loves her, and she doesn't respond accordingly. After talking to Eric, Serena figures out that she probably has trouble hearing that Dan loves her after experiencing her mother's many husbands.

She goes to see him at the loft and he tells her a whole list of reasons that he loves her. Soon after, Serena's old friend Georgina Sparks comes back to the city to stir up trouble. They later resolve their issues, but Serena tells Georgina she no longer wants to be in contact with her. After Georgina blackmails Serena with a video of the night where they witnessed Pete Fairman, a late mutual friend, die, Serena goes off the deep end.

She's rescued by Blair, Nate, and Chuck, who try to keep Dan away from the situation. To keep Dan from knowing what she really did, Serena lies that she cheated on him and he tells her that he is done.

During Lily and Bart's rehearsal dinner, Lily goes with Serena to see the Fairman's and gain closure. Afterwards, Serena goes to find Dan but finds out that he's with Georgina; who is planning to seduce him Woman on the Verge. He then teams up with Blair to get rid of Georgina, which they successfully do.

However, at Lily and Bart's wedding, he breaks up with Serena; not wanting to deal with the drama and struggles of their relationship anymore. While there, he gains CeCe's approval and the two reunite.

However, they break up again in The Dark Night due to their worlds being too different. Jealous, Serena intervenes on one of their dates and decides to ice Dan out of her life. But after awhile, they patch things up and start becoming friendly again Chuck In Real Life. She is unsure at first, both about going and about whether she still has feelings for Dan.

As a result, she asks Dan if he thinks she should go and he tells her she should; a decision she agrees with once she learns their parents are planning to rekindle their relationship. However, she breaks up with Aaron on the plane and when she returns, admits to Dan that she misses him and they get back together.

Soon after, Dan discovers that Lily had Rufus' lovechild many years ago and that she gave the baby up for adoption. Knowing he shares a biological sibling with Serena, he begins to distance himself from her In the Realm of the Basses.

In You've Got Yale! Dan is instantly attracted to her and they strike up a friendship surrounding writing and literature. Meanwhile, Blair decides to take action against Rachel for giving her her first B and ends up with detention after being caught hazing her.

Wanting even more to destroy her, Blair starts a rumor that Dan and Rachel are sleeping together. After Serena spots the two having a seemingly romantic dinner, she takes a photo and gives it to Blair; who shows it to the PTA of Constance and Headmistress Queller. When Serena finds out, she plans to charm Gabriel into giving all the money back but Dan is skeptical her plan will actually work.

Worried about what to do, he informs Lily of the situation and Serena's plan. Lily then orders Serena to stop and when she doesn't, has her arrested for theft The Wrath of Con. In Valley GirlsDan bails Serena out of jail and escorts her to prom. Season Three In Dr.

EstrangelovedSerena reunites with her father, William van der Woodsen. After it's revealed that Lily has been being treated for cancer by him, he decides to move back to Manhattan in the same building as the VDWs.

Dan, Nate, and Blair do not believe this and work with Chuck and Jenny to find the truth behind what happened. They're able to uncover William and Holland's plan to split Rufus and Lily up for selfish reasons. However, Jenny is wanting to return to her life pre-UES and informs William that everyone knows so he can leave town before getting caught.

Serena is able to catch him before he leaves and leans on Dan for support when he does Ex-Husbands and Wives.