20 Things Everyone Gets Wrong About Gossip Girl | ScreenRant
In real life, Blake Lively and Penn Badgley dated and broke up. Or Dan? I mean Gossip Girl? (Sorry, it's just so funny 10 years later.) It's been 5 years since the finale and I'm still absolutely raging that Dan turned out to be Gossip Girl cheating on her with Georgina, dating her best friend, writing a satire about her, AND being Gossip Serena Celia (née van der Woodsen) and Daniel Randolph Humphrey These photos of Blake and Ed are my faves!!. Dan is visibly surprised to read a Gossip Girl update saying that Serena's looking for a date to the masked ball, and decides to blow off his.
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.
I'm dating again at 45 – and I just love it!
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.
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.Blake Lively Remembers The Night Ryan Reynolds Fell For Her - PEN - People
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?
I'm dating again at 45 – and I just love it! - trinamichaels.info
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.
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.
In the finale Much 'I Do' About NothingSerena confesses the whole truth to Dan, To get back at Georgina, he works with Blair to send her away from the city by sending her to boot camp.
At Lily and Bart's wedding, he breaks up with Serena, not wanting to be around the drama and problems that come with the differences in their worlds. Season Two Beach In the premiere Summer Kind of Wonderfulit's revealed Dan spent the summer interning with Jeremiah Harris and dating multiple women to get over his break up with Serena.
However, he realizes he misses her and goes off to find her in the Hamptons. At the party, he makes up with Serena and they spend the night on the beach together. Soon after, Dan returns to the city but keeps hooking up with Serena, eventually deciding to get back together Never Been Marcused.
After a little while, they realize once again that they come from very different worlds and that it just isn't going to work between them. They talk after being trapped in a elevator during a black out, and break up again The Dark Night. On the first day of school, Dan and Serena act awkwardly to each other but agree to try and be friends.
He meets a new girl, Amanda Lasherand they go out together. Blair, not wanting Serena to get hurt, plots to split Dan and Amanda up. Dan, wanting to go to Yale, tries to get Noah Shapiro to write him a recommendation. He encourages Dan to get out of his comfort zone, so Dan begins hanging out with Chuck. He learns all sorts of personal things, such as that Chuck believes he killed his mother because she died during childbirth.
On one of their outings, Chuck mistakenly assumes a woman is an escort and is threatened by her boyfriend. To stop the escalating fight, Dan punches the guy but gets both of them arrested for brawling in public. Chuck thanks him for having his back but takes it back after learning Dan was writing about him. During a visit to Yale, Nate, knowing everyone there hates his father for his crimes, pretends to be Dan.
Dan Humphrey - Wikipedia
Meanwhile, Dan finds out he needs another recommendation and runs around campus trying to get it. He's directed to a girl named Jordan, who Nate is hooking up with for the weekend. Dan reveals that Nate is lying about who he is, but gets his work submitted. Meanwhile, Chuck is kidnapped by a secret society who promise to let him in if he brings Nate to them.
Not wanting to hurt his best friend, Chuck tells them Dan is Nate. After returning to New York, Nate invites Dan to play soccer in the park.
Dan mistakingly assumes they're meeting at Nate's townhouse and goes over.
He finds that Nate is living with the bare minimum after his family lost all their money. He tells Jenny, who suggests he invite Nate over for dinner to convince him to stay. While at dinner, he reveals to Nate that he knows how bad he's living, but Nate orders him to stay out of it. After running into Serena on the street, they begin to rebuild their friendship and she tells him that he's a good friend for Nate.
Dan encourages her to, and gives her enough confidence to do it. However, he learns that recently Chuck and Blair used Vanessa in one of their games and decides to instill doubt in Blair over what Chuck will say. As a result, Chuck and Blair are more at odds than ever. Serena admits to Dan that she genuinely thought he could help Blair be brave. Dan realizes he messed up and tells Chuck that Blair was going to reveal how she felt until he stopped her.
In Bonfire of the VanityDan is hired to find inside information on Chuck's dad, Bart, to use in a magazine. He starts hanging out with Bart, pretending to be interested in his business, but Chuck is suspicious. After meeting with a source, Dan discovers that Bart burnt down a building years ago to collect insurance money. Chuck tells Bart that Dan is planning to expose him, then asks Dan to not to.
Dan decides to send Bart the story he wrote about Chuck, where he felt responsible for his mother's death, and it results in the Bass men becoming closer. Meanwhile, Serena has begun dating Aaron Rosean artist whose work is displayed at Rufus' gallery, but isn't revealing her party girl past. On Thanksgiving, Dan mentions the Georgina thing to Aaron, and Serena becomes mad that he revealed some of her secrets to him.
He agrees to take her to the Snowflake Ball as his date, and Serena discovers that Lexi sleeps with guys on the first date.
She debates whether to warn him, and does so at the dance. After a brief argument, they tell the other that the first time they had sex was the greatest night either has ever had. After Bart's funeral, Dan realizes he still has feelings for Serena and attempts to tell her at Eleanor and Cyrus Rose 's wedding. When school resumes, Serena reveals to Dan that she broke up with Aaron and that she still loves him. They agree to get back together, but their happiness is short lived when Rufus is not supportive.
They hunt for clues as to why, but find none. He tries to keep it hidden from Serena, but tells Vanessa. After the dust settles, Dan admits to Serena that he really did want to tell her but Rufus made him not. They decide to make it work despite the revelation Gone with the Will.
Dan gets accepted into Yale in You've Got Yale! He also meets her new Shakespeare teacher Rachel Carrwho he begins to hang out with. The two grow close, bonding over their mutual interest in literature and writing. Blair, who is given detention after hazing Rachel, exacts revenge by spreading a rumor that Dan and Rachel are having an affair. While at dinner, Rachel is extremely upset with the news and Dan hugs her to comfort her.
Outside, Serena witnesses the event and tells Blair, who informs the Parent Committee. While Blair is meeting with them, Dan and Serena break up. The committee votes to fire Rachel, and after it's done, she and Dan sleep together Carrnal Knowledge. Rachel shows up at rehearsal for the senior play The Age of Innocence, and she and Dan correspond in notes.
They make plans to meet up at her apartment, but Rufus intercepts the note and goes in Dan's place. Right before opening night, Dan and Rachel have sex in the costume closet. After the performance, he discovers Rachel told Yale that she was hazed by Blair, costing her her acceptance.
He ends things with her, and she returns to Iowa The Age of Dissonance. Soon after, Rufus discovers that Dan won't receive financial aid from Yale.
He confesses to Vanessa, who tells Dan Remains of the J. Wanting to help out, Dan gets a job as a cater waiter but ends up serving the Waldorf Seder. While working, Serena, having just returned from Spain with Poppy Liftonis worried she accidentally married Poppy's boyfriend Gabriel Edwards.
She confides in Dan after he overhears her talking with Cyrus, and when Gabriel shows up to the dinner, they pretend they're back together Seder Anything. After Gabriel and Poppy's con scheme is revealed, Serena decides to fix the problem herself. She tells Dan, who knows that Rufus invested his college money with Gabriel. He decides to tell Lily, who orders Serena to back off.
When she doesn't, Lily has her arrested The Wrath of Con. On prom night, Serena is still in jail but Dan bails her out to escort her Valley Girls. Serena vows to find her identity to stop her, but fails. When she sends the text asking Gossip Girl to meet her, Dan is the first to show up. Once summer begins, he hears from Georgina, who has gotten Rufus' money back and who will also be attending NYU in the fall. He also meets Scott Rossonalthough he introduces himself as Scott Adler.
Dan meets up with Vanessa, who feels he's becoming another shallow Upper East Sider. Her new friend Scott encourages her to tell Dan what she thinks at the van der Bilt polo match, and she agrees. On the first day of NYU, Dan instantly fits in and makes new friends. Blair, who is determined to rule the school, asks him to take her to Georgina's rooftop party.
He does, but quickly learns it was a mistake when Blair humiliates Georgina in front of everyone. Dan sticks up for Georgina, and gains more popularity. At the end of the night, he ends up sleeping with her The Freshmen. However soon after, he tells her that he isn't interested in her.
At her movie premiere, he realizes who she is but decides he likes her too much to end things with her. Upon learning Dan is dating Olivia, Georgina blackmails Vanessa into trying to break them up. When Dan catches her, she admits that she knows that Scott is her brother.
Meanwhile, Rufus and Lily are planning their wedding for the next day and Vanessa tells Dan to hold Georgina off for as long as possible. He pretends to want another chance with her, but she figures out he's lying. On wedding day, she brings Scott to town and reveals his identity to Rufus and Lily. To get her out of the picture, she tells Olivia that Dan is embarrassed to introduce her to his parents, and she tells Dan that Olivia is anxious about meeting his parents.
They believe her, until the dinner when they figure out Vanessa played them Enough About Eve. Meanwhile, Serena has taken a job with Olivia's publicist KC, and wanting to help make Chuck's party a success, she asks Olivia to walk the red carpet with her ex Patrick Roberts. Olivia agrees, but Dan is uneasy as he's seen their sex scenes and knows about their past relationship. When the party is broken up due to a fake liquor license, they reveal their relationship to the press How to Succeed in Bassness.
After a Jimmy Fallon appearance, Olivia tells a story about her first date with Dan, and how he came back from the restroom at one point with his shirt on backwards, claiming a spider climbed inside. Jimmy dubs Dan "Bathroom Boy", and Olivia tries her hardest to prevent Dan from seeing the interview.
However, he ends up seeing it and while watching the segment, remembers it's their one month anniversary. He heads home to plan a special night for them The Grandfather: In an attempt to get her to stay, Dan and Vanessa take her to complete a bucket list of things all college students need to do.
The list ends with having a threesome, which the three engage in. Soon after, the awkward results begin to show; causing Vanessa and Olivia to fight over who Dan "belongs" to.
Olivia confesses to Dan that during the act, he was looking at and kissing Vanessa with passion he never had with her. She breaks up with him and leaves, promising to come back the next fall The Last Days of Disco Stick. On Thanksgiving, Vanessa's mother Gabriela Abrams comes to town. After observing Dan and Vanessa, it becomes clear to her that Dan has feelings for Vanessa. She warns him to only tell her his feelings if he's serious about her, because their friendship won't survive another heartbreak The Treasure of Serena Madre.
After Serena's car accident, Dan and Vanessa go to the hospital together and he reveals that he loves her, but she rejects him The Debarted. Soon after, the two end up at a party thrown by Vanessa's dorm with dates to make the other jealous. After awhile at the party, they kiss and decide to try and make a relationship work The Lady Vanished. Not wanting to jeopardize things, they agree to hide from everyone else at first. At a brunch, Serena and Nate congratulate them, but warn them not to fall into a rut.
Vanessa takes the advice seriously and plans a homemade dinner based off of one of Dan's favorite movies. The dinner is awkward, and is eventually crashed by Rufus at accident. After the debacle, Dan goes to see Vanessa at her dorm and tells her that just being with her is special and not boring The Empire Strikes Jack. Dan applies to Tisch for their screenwriting program, and he and Vanessa agree to read each other's screenplays. However, this process proves more difficult than anticipated when they're not sure how honest they can be with each other.
EstrangelovedDan is rejected from Tisch and finds out Vanessa took the one transfer spot. She offers to drop out, but Dan tells her not to. He admits to Willa Weinstein that Vanessa's submission was a piece based on one of his stories, and Willa decides to use this information to get Dan in and Vanessa out.
Dan eventually finds out that Vanessa applied with an original piece, so he tells Willa to undo what she did. She refuses, but Dan holds his ground. Not too much later, Dan finds out Vanessa was offered an internship in Haiti. Their plan works, but Serena becomes angry that none of her friends will accept her father.
After she realizes they were right, she follows him to the airport and lets him go. It's revealed that Dan went with her for support Ex-Husbands and Wives.