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At a privileged prep school for teens on Manhattan's Upper East Side, the students first learn that Serena van der Woodsen is back in town the way they learn all the important news in their lives: from the Internet blog of the all-knowing, albeit, ultra-secretive 'Gossip Girl'. No one knows Gossip Girl's identity, but everyone in this exclusive and complicated vicious circle relies on her website and text messages for the latest scoop. Even Serena's closest friend, Blair Waldorf, is surprised to find that Serena has suddenly ended her self-imposed exile from a boarding school in New England and returned to Manhattan for school. Once the Upper East Side's most notorious party girl, Serena's reasons for returning are mysterious, although they may have something to do with her younger brother Eric, who's secretly in the hospital following a suicide attempt which is kept under wraps by their overprotective mother Lily. Whatever the reasons, the change in Serena is obvious, especially to Blair, whose friendship with Serena has always been competitive and difficult. Into this crowd comes Dan Humphrey, a kid from Brooklyn and whose freshman sister, Jenny, tries a little too hard to fit into Blair's circle of gossip friends, whom include 'Gossip Girl's contacts, Isabel and Kati. Blair's nice-guy boyfriend, Nate Archibald, is also troubled by Serena's return for his best friend, Chuck Bass, the school's snobbish cynic and resident bad boy, knows about a fling that Serena and Nate had which is why Serena left town to avoid a scandal which, in the snobbish world of high society, is social suicide. Elsewhere, Dan and Jenny's father, Rufus, a former rock musician and art gallery operator, also has a return of feelings for Serena and Eric's mother, Lily.
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Serena confides in Blair that she had sex with her boyfriend, Nate, right before she skipped town. But Blair, being the person she is, vows a cruel revenge against Serina who decides that Dan would make a good escort for the fund raiser brunch at the Palace Hotel... a brunch hosted by none other than Jenny's would-be rapist, Chuck, and his uptight father Bart. Meanwhile, 'Gossip Girl' posts on her web bloc that Jenny, the eager freshman, paid a visit to ultra-cool Blair, who quickly realizes that granting the eager wannabe access to her elite inner circle might just prove useful. Elsewhere, Lily meets with Rufus about how their lives went since they parted 15 years earlier, and Dan discovers Lily's relationship with Bart, while Blair sends him running after she tells him all about Serina's sordid past.
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Blair is thrilled when her mother, Eleanor, chooses her to be the new face of her clothing line. However, Blair's happiness soon turns to her typical feelings of betrayal and jealousy when Serena moves into the spotlight and Blair finds herself back in Serena's shadow. Meanwhile, Serena and Dan are reminded once again that they come from two very different worlds, and Nate and Chuck indulge in a boys' weekend with the former trust-fund case, Carter Baizen, to blow off steam after Ivy Week, and who gets the guys into trouble with some of his poker player thugs. Elsewhere, Rufus bonds with an attractive art collector, named Bex, whom is interested in his latest painting at the Bedford Avenue Art Gallery where he works.
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Dan makes elaborate plans to impress Serena on their first official date. That same night, Jenny is invited to the infamous Blair Waldorf sleepover and finds herself in a high stakes game of "truth or dare." Meanwhile, when Lily discovers that Eric is missing from his treatment center, she finds herself seeking help from her ex-boyfriend, Rufus.
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Although it is Thanksgiving, hardly anyone has the holiday spirit. Blair and Serena have a fight once Serena admits that she saw Blair with Chuck, and Blair orders Serena to keep it to herself. Meanwhile, Nate and his family share a strained Thanksgiving meal before Mr. Archibald ends up in the hospital after a suicide attempt. Having been uninvited by Blair to the Waldorf Thanksgiving meal, the Van der Woodson family has dinner with the Humphreys at their loft in Brooklyn, and the tension between Lily, Allison, and Rufus is palpable. Back in Manhattan in the Waldorf penthouse, Blair revisits her bout of bulimia after discovering that her mother forbade her father to join them for Thanksgiving. Throughout the entire episode, there are flashbacks of last year's Thanksgiving involving how Dan met an stoned Serena for the first time as well as Blair's Thanksgiving with her father and mother before their seperation. There is a stark contrast between its joy and the present's strife.
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As 'Gossip Girl' posts news of the annual Cotillion Ball to take place on the approaching weekend, Blair decides not to go with Nate, but she finds herself being featured in The New York Times and is enjoying her secret affair with Chuck. Serena decides not to go either, so her grandmother, CeCe, shows up to change her mind. Meanwhile, Jenny volunteers for the ball and Lily takes her under her wing. But the night of The Cotillion is the night of Alison's first art opening, and Rufus and Alison tell Jenny that she cannot attend the ball. Jenny decides to defy them both by secretly attending the dance anyway. Refreshed by Blair's newly buoyant attitude, Nate asks her to the Cotillion and she accepts, which makes Chuck jealous. CeCe tells Lily and Serena that she is sick with lung cancer and her last dying wish is to see Serena go to the ball, and she wants Serena to go with the wealthy Carter Baizen. The snobbish CeCe takes an instant dislike to Dan and she approaches Rufus with an offer pay him to convince Dan not to go with Serena. Dan learns of this and tells Serena that he does not think very highly of CeCe by telling Serena about how CeCe tried to bribe his father to persuade him not to attend. Surprisingly, the skeptic Serena refuses to believe Dan that her compassionate grandmother is a crafty snob, and she ends up going to the ball with Carter... both her and Dan having fallen right into CeCe's ploy. Also, Chuck manipulates Nate into thinking Carter is having an affair with Blair to provoke a fight with him.
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Blair's estranged father, Harold, comes home for the Christmas holidays with an unexpected guest: his gay lover Roman. Both Blair and her mother, Eleanor, find it difficult to hide their disappointment while Blair hatches another underhanded plan to get rid of Roman for good. Meanwhile, Jenny and Vanessa help Serena plan the best Christmas surprise ever for Dan, who may have a surprise of his own in mind for Serena. Chuck phones Blair from Europe and informs her that Nate has joined him in Monaco, worrying Blair that Chuck may disclose the details of their hook-up. Also, Rufus refuses to remain the understanding husband any longer after Alison's former lover calls the house.
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Blair is against the idea of her mother, Eleanor, with a new man in her life, named Cyrus Rose, and she in her natural and evil ways, does everything in her power to make it impossible for them to be together. Meanwhile, Jenny and Agnes move in together into their own apartment, against Rufus protest. Serena and Aaron fall for each other, but something about Aaron threatens to ruin their new relationship. Elsewhere, Dan and Chuck are at war due to Dan's true interest in Chuck's father Bart.
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As Thanksgiving draws near, Blair looks forward to spending the holiday with her family. But her disappointment only begins when her father, Roman, is delayed in trying to leave Europe, and her mother's new boyfriend, Cyrus, takes over planning the traditional Thanksgiving feast. Blair also learns that Cyrus plans to propose marriage to Eleanor, which prompts her to run into the company of her Polish maid, Dorota. Serena continues to hide her sordid past from Aaron after he tells her that he too is a recovering alcoholic and party guy. Meanwhile, Dan asks Lily to help intervene in the continuing feud between Jenny and Rufus when she decide to file a petition to become legally emancipated from her father. Eric also learns from Chuck about Bart's investigation and files he keeps on everyone to keep everyone and everything under his iron thumb. Elsewhere, Nate's fugitive father arrives in town to visit him and his mother with an offer to live a life of luxury as fugitives, while Vanessa gets caught up when the authorities comes to call her on Mr. Archibald's whereabouts after he's spotted re-entering the country.
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As Constance Billiard prepares for the annual school play of 'Age of Innocence' the frantic production threatens to break the whole school apart as, Dan continues to ignore Serena and continue his dirty tryst with Rachel Carr. When Blair learns that her acceptance into Yale went to Nelly, she suspects Serena of leaking info about her detention stint, while Serena blames Blair of babbling about her own problems. But the real culprit it Rachel who is seeking to get back at Blair for destroying her career. Rufus and Jenny learn about Dan's relationship with Rachel Carr and try to force him to end it. Nate becomes jealous when he thinks that Vanessa is flirting with the play director Julian, while it is Serena who has the crush and asks Vanessa for pointers Meanwhile, Chuck becomes more intrigued and frustrated as he tries to dig deeper into the mystery about his late father and what connections he had with the super-secret underground society which leads him to try to find the shadowy Elle, who warned him about investigating the secret society.
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Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf existence in favor of a wild, unpredictable lifestyle that includes Carter, causing Serena and Chuck to have serious concerns about their friend. Vanessa convinces Nate that it may be time to forgive and forget when it comes to his mother's Kennedyesque family, The Vanderbilts, who abandoned Nate and his mother when they needed them most. Elsewhere, in a misguided effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers.
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Serena decides to throw Jenny an intimate party for her 16th birthday, but things get out of control when Serena's friend Poppy Lifton, returns and turns the small gathering at the van der Woodsen apartment into a huge social event. Meanwhile, Vanessa agrees to help Chuck with a scheme that will make Blair and Nate jealous... and they end up having have sex in the process. Also, Rufus learns that Dan and he will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education, in which Lily offers to help. Elsewhere, Dan receives a letter from Boston from Rufus and Lily's illegitimate son wanting to meet with him.
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Serena returns from her week-long trip to Spain with Poppy and Gabriel. But Serena becomes worried that during the hard partying in the country, she thinks she may have gotten married to Gabriel by accident. Meanwhile, Blair makes a secret deal with Nate's grandfather, William, to influence Nate to attend Yale when he decides to defy his grandfather and attend Columbia University in New York City instead. Later, Nate learns some disturbing information about his father's arrest while he is asked to be the best man at his cousin Trip's upcoming wedding. Chuck continues his debauched lifestyle of one-night stands while Jenny decides to make a stand for herself against the loathsome guy. Elsewhere, Dan takes a job as a waiter to earn money for college. H is distressed to find out that the job is a Passover Seder at the Waldorf penthouse that Cyrus holds, and on top of that... several of his friends and family are guests, including his father Rufus.
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Georgina Sparks returns to the Upper East Side after undergoing a major transformation. Chuck and Nate find themselves at a major crossroads in their relationship as it pertains to their mutual interest in Blair. Serena finds her relationship with Gabriel growing more complicated, when Blair and Chuck discover is still with Poppy. Meanwhile Dan and Vanessa will get drunk playing "I never ..."
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Lily recalls her past when in a flashback to 1983, the naive and sheltered 17-year-old Lily Rhodes got kicked out of her boarding school. She ran away to Los Angeles where she tried to re-connect with her divorced and dysfunctional parents; her workaholic record producer father, Rick Rhodes, and the superficial Cece. Lily also met and hooked up with her outgoing free-spirited 19-year-old sister Carol. Carol was the so-called "black sheep" of the family who introduced Lily to the life of partying, as well as Owen, a busboy at Carol's place of employment. They all got arrested after crashing a party hosted by the cynical and mean music producer Keith van der Woodsen (Lily's future husband) whom attempted to swindle Carol out of a music deal. In present day New York, Blair and Nate decide to attend their senior prom together. But the evening doesn't turn out exactly as planned, when the Mean Girls attempt to rig the votes for prom king and queen. But Chuck comes to Serena's rescue. Meanwhile, Serena becomes furious when she learns that Lily deliberately had her arrested for her defiance, while Rufus ponders his life and future without Lily, who he snubs for what she did to Serena, as does Eric, Jenny, and even Dan as well whom is forced to bail Serena out of jail himself.
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Gossip Girl decides to liven things up at the Constance Billard and St. Jude's graduation by sending out a shocking and damaging email blast in the midst of the commencement ceremony, stirring Serena to come up with a plan of attack. The Mean Girls (guest stars Yin Chang, Nicole Fiscella, Amanda Setton and Dreama Walker) challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year. Lily and Rufus get engaged and move in together. With Blair's blessing, Jenny becomes the new queen. Chuck finally admits his love to Blair and the two reconcile. Nate decides to go on the backpacking trip with Vanessa, while Georgina recovers Dan's money and requests Blair for a roommate at NYU. Carter Baizen reveals to Serena where her father is. In the end Serena is going to Brown, Blair, Dan, Vanessa, and Georgina are going to NYU, and Nate is going to Columbia.
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As the summer is drawing to a close, Blair and Chuck are madly in love and adjusting to their new "in a relationship" status, breaking all the traditional rules of dating as would be expected. Serena returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen. Nate returns from his travels with a mysterious brunette, Bree Buckley in tow. Rufus, Dan and Jenny spent the summer in the Hamptons, adjusting to the van Der Woodsens' glamorous lifestyle surprisingly faster than any of them expected. Meanwhile, Vanessa begins a relationship with Scott, not knowing that is the lost brother of Dan and Serena.
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Blair, who is determined to maintain her Queen status in college, embarks on her first day at NYU, along with Dan and Vanessa. Unfortunately, Georgina turns up as Blair's roommate in the dorms, determined to make Blair a social outcast. As Serena prepares to depart for Brown, she and Chuck have a major falling out, so she recruits Chuck's enemy, Carter, to help her get even. Nate and Bree decide to explore their relationship further, knowing full well that it could cause tension between their families who are political rivals.
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It's an Upper East Side face-off when Blair and Chuck both set their sights on a particular item up for bid at Sotheby's and the personal stakes are high. Serena suspects that Carter may be up to his old habits, Georgina takes an interest in Dan, and Vanessa begins to suspect that something isn't quite right with Scott.
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On the first day of school at Constance Billard, Jenny is forced to make her rightful place as the new Queen Bee of the Mean Girls. Unfortunately for Jenny, Blair is more than happy to intervene when news reaches her that Jenny may need her help. Meanwhile, Lily finally returns home to Rufus and her family to find that things are definitely not as she left them, especially after learning that Serena has decided against going to Brown University. Elsewhere, a famous teenage movie actress, Olivia Burke, enrolls at NYU and is assigned as Vanessa's new roommate in which Olivia hopes for a somewhat normal college experience. Also, Olivia's best friend Ursula, another actress co-starring in Olivia's latest movie, befriends Serena.
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Lily and Rufus decide to move up their wedding to the next day, but a series of complications threaten to tear them back apart again. Meanwhile, Chuck discovers a secret that Carter has been keeping from Serena which involves Nate's girlfriend Bree and her family whom are out to get Carter. Dan and Vanessa are pulled into one of Georgina's schemes when she threatens to ruin Lily and Rufus' wedding by revealing the secret about Scott Rosson as their illegitimate son. Also, Blair is suspicious of Bree and shares her concerns with Nate that she may have an agenda regarding him and Carter.
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Vanessa hopes to win over her stern and estranged mother Gabriela's approval when she desperately vies with Blair for the honor of delivering the freshman toast at NYU. Meanwhile, Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple, as well as the newlyweds. Also, Serena and Nate team up to help Carter Baizen by going to an underground gambling casino to win money to pay off the Buckley family whom have exiled Carter to Texas to work off his debt to them.
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Chuck decides to move up his hotel nightclub's opening and enlists Serena's help to get the word out to her celebrity clients for publicity reasons. Feeling left out of the planning, Blair attempts to win Chuck's approval by secretly helping him with a problem concerning opening night. Meanwhile, Dan is unnerved when he finally watches one of Olivia's infamous simulated sex scenes in one of her movies with co-star and real-life boyfriend at the time, Patrick Robinson. Jenny is forced to choose between her friendship with Eric and her new role as Queen Bee of Constance Billiard since she and the Mean Girls are not required to have any friends, except the ones their own vicious and cynical circle. Elsewhere, Rufus gets Lily into the Halloween spirit by taking her out to a costume party.
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Olivia says something she regrets during her appearance on Jimmy Fallon's TV talk show and tries to keep Dan from finding out. With the local election day around the corner, Nate suspects that his grandfather will stop at nothing to get his cousin Trip elected to congress. In the midst of another feud with Serena, Blair befriends a new "it" girl and takes her to an election night party at Chuck's hotel, hoping to make Serena jealous.
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Hoping to impress the elitist theater kids at NYU, Blair sets her sights on landing a private concert with the hottest musical performer of the year, Lady Gaga. Meanwhile, Dan and Olivia sign up to write and star in a school play, based on an idea by Blair and directed by Vanessa. With Blair out of the picture, Serena turns to Nate to help her get through a difficult situation. As a favor to Chuck, Jenny agrees to hang out with Damien, the son of an ambassador who is staying at Chuck's hotel, but the experience proves to be a lot more intriguing than she expected.
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As Thanksgiving draws near, Blair suspects her mother, Eleanor, has been keeping a big secret from her, but it turns out to be something else entirely. Meanwhile, Vanessa is supposed to spend Thanksgiving with her parents, but has a fight with her picky and estranged mother and she ends up going to Dan's loft. Rufus discovers that Lily has been lying to him about the true nature of her mother Cece's health. Chuck tells Nate that he has some potentially damaging information about one of their friends: Serena whom is caught in a compromising position with Trip Vanderbilt. Elsewhere, Jenny learns that Eric was behind her very public embarrassment at Cotillion and can't pass up a chance to get even with him in the most cruel way, which makes her appear even more vile and twisted than everyone else around her. Also, Serena is put in a very awkward position when Lily invites Trip and his wife, Maureen, to join them for Thanksgiving dinner at their penthouse, and Maureen may know a lot more about what is going on between Trip and Serena than she claims to, and Doroda is revealed to be hiding a secret of her own involving Vallini.
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Nate and Serena decide to explore the boundaries of their friendship. Blair suspects that Chuck is having problems forgetting about the woman he saw at his father's grave. Jenny agrees to accompany Damien to a State Dinner but is unaware that he needs her help with a drug exchange. Vanessa and Dan attempt to move past the awkwardness of Dan's confession of love. Rufus returns from a ski trip and tries his best to avoid Lily.
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Rufus and Lily grow suspect of JennyÂ’s relationship with Damien. Chuck learns more about the woman who may or may not be his mother. Dan and Vanessa struggle through the awkwardness of dating other people.
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Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have sex with her. Lily tells Rufus the big secret she has been keeping from him even though she knows itÂ’s a huge risk. Dan and Vanessa explore a new stage of their friendship. Chuck is forced to make an extremely difficult decision about his hotel.
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Chuck finds himself once again at odds with his uncle, Jack Bass. Eleanor puts Blair in charge of making sure her latest fashion show is a huge success with an important client. Rufus attempts to get Jenny back on track by volunteering to have her help with EleanorÂ’s fashion show, but the opportunity takes a big turn for the worse when Jenny learns that Agnes will be one of the models.
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Chuck and Blair are faced with the most difficult decision they have ever faced as a couple. Serena plans a surprise birthday party for Nate, but Jenny does her best to sabotage SerenasÂ’s efforts. Dan and VanessaÂ’s new relationship hits a bump in the road.
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Chuck offers to throw a wedding for a very pregnant Dorota who insists that she and Vanya have a traditional wedding before her parents arrive from Poland and find their daughter pregnant and without a husband. Dorota asks Blair and Chuck to be part of the ceremony and walk her down the aisle. Serena tells Nate she is having breakfast with the Humphreys when in reality sheÂ’s secretly meeting up with Carter Baizen. Rufus discovers that Lily has been lying to him about her whereabouts.
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When LilyÂ’s ex-husband, Dr. William van der Woodsen, shows up unexpectedly in Manhattan, Serena finally gets the reunion she has so desperately wanted with her father, but the circumstances turn out to be far from ideal. When Serena and Nate continue to have relationship issues, a scheming Jenny is more than happy to be a shoulder for Nate to lean on. Meanwhile, Dan finds out that he didnÂ’t get accepted into the Tisch writing program and Vanessa admits she may have been somewhat responsible.
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WillÂ’s return to the Upper East Side continues to stir up problems for Serena, Lily and his long-standing rival, Rufus. Serena and JennyÂ’s relationship is strained as a result of JennyÂ’s deception. Blair spends time on the Columbia campus and realizes where she truly belongs. Dan learns that Vanessa has been keeping yet another secret from him.
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When things get tense between Rufus and Will, Serena chooses to stand behind her father, while at the Rufus is made to feel like an outsider in his own family. Meanwhile, Jenny deliberately shares information with Will that may ultimately destroy Lily and Rufus’ marriage. After many failed attempts, Chuck makes one last grand gesture to reconcile with Blair, hoping she will finally accept the fact that they are destined to be together.
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Blair must decide whether to meet Chuck at the top of the Empire State Building or risk losing their future together. A Gossip Girl gossip bomb involving Dan explodes Serena and Nate’s relationship. Dorota and Vanya welcome their baby. Jenny hits rock bottom. Georgina returns to the Upper East Side…and she has an agenda.
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The end of summer is approaching in a few short weeks and the aftermath of what happened last year has changed everything. A radiant Blair and Serena are enjoying their grand, romantic summer in Paris before they both have to return to New York. Despite their french flings, they're amazing vacation comes to a halt when Chuck mysteriously arrives in town with a new girlfriend and a new identity. Blair convinces herself that she's sworn off Chuck forever after he slept with Jenny, but Chuck seems to be a changed man and woos Blair into having a change of heart, but Blair isn't sure if she fall for him again and wonders if she should set her sights on ruling Columbia University instead. Meanwhile back in New York, Georgina gave birth to her baby and has convinced Dan he is the father. Dan contemplates telling Rufus but he can't and keeps it a secret. Vanessa who is back from Haiti seems to accept Dan playing Daddy, but is still having mixed feeling about getting back together. Nate, still hung up over Serena, tries his best efforts to ignore his feelings by dating Juliet, a Colombia student.
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Serena tries to convince Chuck not to change his name or his identity. While Blair falls for a parisian prince, she still has feelings for Chuck, which leads to Blair makes a decision about riding off into the distance with her Prince, or going to see her true love who broke her heart. Also, Blair gets into a dispute about a college issue with Serena when she hears Serena may be going to Colombia. In New York, Dan continues to take care of Georgina's baby, but begins to have doubts the kid is in fact his child. Vanessa feels the same and hatches a scheme to find out if Georgina is lying. Nate and Juliet's flirtation brings them closer and Juliet tries to help Nate forget about Serena altogether.
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On her first day at Columbia, Blair attempts to gain membership into an ultra-exclusive social club, Hamilton House, but she's in for a few big surprises. Serena begins to suspect that Juliet is intentionally sabotaging Serena's life and that it may have something to do with Nate. Rufus is worried about Dan and decides to take matters into his own hands.
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Nate suspects that Juliet is keeping a big secret from him and decides to confront her. Blair schemes to undermine Chuck's newfound happiness. Dan finds himself torn between his feelings for Serena and Vanessa.
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An anonymous Gossip Girl blast starts a very damaging rumor about one of Columbia's new students, Serena. On her path to greatness, Blair decides to take a class with a powerful businesswoman, Martha, who is guest-lecturing at Columbia, but a mysterious fellow student thwarts her plans to secure the prized position as Martha's assistant.
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Although Blair made it perfectly clear that Little J was no longer welcome in Manhattan after what happened with Chuck, Jenny is tempted by a once-in-a-lifetime opportunity to meet Tim Gunn, which could be a game changer for her future. Meanwhile, Serena discovers something about her new boyfriend, Colin, that may put an end to their relationship just as it was getting good.
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Blair is caught off-guard - and not in a good way - by a surprise guest at her birthday party. Having had enough of Chuck and Blair's games, Serena and Nate decide to plan an intervention.
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Chuck and Blair decide it's in both their best interests to put the past behind them and end their vindictive games. Nate confronts Juliet after discovering a secret she has been keeping from everyone. Dan and Nate realize they both still have feelings for Serena.
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Chuck hosts a "Saints and Sinners" masquerade party at the Empire Hotel. At the party, Dan and Nate don't know what to make of Serena's strange behavior and mixed messages. Blair sets her sights on becoming the new face of Anne Archibald's foundation for girls, but Anne is concerned that Blair's friendship with Chuck Bass may be problematic.
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This synopsis is too short and may not include the required detailed description of the entire plot. We normally require that synopses be at least 10 lines long. If you have seen this title, please help us by improving and expanding this synopsis. Chuck, Serena, Blair, Dan, Jenny and Eric find themselves faced with a crisis when a member of one of their families is hospitalized on Thanksgiving. Meanwhile, Nate attempts to help his parents reconcile.
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Blair and Dan join forces to track down an MIA Juliet. Chuck begins to suspect Lily isn't telling him the full truth. Kevin Zegers guest stars as Damien.
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A former associate of Chuck's father, Russell Thorpe - along with his daughter Raina - returns to Manhattan with some unfinished business for our Upper East Siders. Serena and Chuck join forces against Lily. Blair realizes that her mother, Eleanor, may be her key to becoming a future CEO. Nate worries that his father, The Captain, is having a little too much fun and not taking his parole seriously.
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Blair is ecstatic to land an internship at W Magazine, but the thrill quickly fades when she finds out that Dan has secured one of the coveted positions as well. Chuck may have finally met his match with Russell Thorpe - and his daughter Raina - back on the Upper East Side. Nate receives alarming news about his father's business prospects.
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Blair enlists Nate's help to win over her high-strung boss, Epperly, at W Magazine. Damien stirs up more drama on the Upper East Side. Chuck finds himself torn between business and pleasure. Florence and the Machine performs an acoustic version of "Cosmic Love."
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It wouldn't be a proper Upper East Side party without some major Gossip Girl drama, and for Eric's 18th birthday celebration there is plenty to go around. Blair decides to speed up the time table on her career path to becoming a powerful woman, but ultimately stretches herself too thin. Serena is forced to choose between her family and Ben. Chuck and Lily's relationship remains icy in the aftermath of Lily's betrayal.
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Ben's mother comes to town, forcing issues to the surface between Ben and Serena. Russell Thorpe is determined to destroy Chuck's family legacy, but he risks alienating his daughter, Raina, in the process.
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As Lily awaits the consequences of her decision, William van der Woodsen, CeCe and Lily's sister, Carol, come into town to support her and be part of a Taschen photo shoot on "modern royalty" in which the Rhodes family is participating. Unbeknownst to Carol, who has always chosen to keep her daughter Charlie far away from the Upper East Side, Charlie has followed her to New York to meet Serena and the rest of the family. Blair has an epiphany about her future, and grapples with the knowledge of whom she's destined to be with.
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Serena enlists Charlie to go undercover Gossip Girl-style to determine why Dan and Blair are spending so much time together, and what role an unexpected visitor is playing in their lives. With Nate's help, Raina decides to go on a search for her long-lost mother. Chuck's hopes about his legacy are dashed with the reveal of devastating information from the past.
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Blair's dreams appear to be coming true, but Serena threatens to jeopardize it all by dredging up Blair's past. Charlie befriends Vanessa, who may or may not have a hidden agenda. Nate is torn between his relationship with Raina and a truth he must keep hidden out of loyalty to Chuck.
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Charlie is finally starting to feel less like a fish-out-of-water with Serena and her friends, but complications present themselves when Charlie is invited to attend the Constance Billard alumni fundraiser. On the road to "happily ever after," Blair finds herself torn between the men in her life. Jack Bass' return to the Upper East Side sets off a chain of events that could end up destroying Chuck and those closest to him.
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Serena loves her new job in Hollywood, but makes a costly misstep when she tries to impress her boss. Chuck and Nate arrive in Los Angeles as the last stop of their Lost Summer trip, joining Serena at a glamorous Hollywood Hills party, where Nate meets a sexy older woman. Blair and Louis return from Monaco and begin planning their royal wedding, but when Louis refuses to stand up to his family and support Blair's choices, his weakness threatens their relationship. A magazine is planning to run an excerpt of Dan's book until an unlikely ally steps in to help him kill the story.
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Nate reconnects unexpectedly with Diana, who offers him an exciting opportunity. Serena forces Charlie to decide which world she wants to embrace. Dan seeks out Chuck's help to stop the publication of his book, but discovers it is Chuck who needs the help. Blair's future sister-in-law, Beatrice, arrives from Monaco, but her motives with Blair may be more than just to get acquainted.
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Nate must decide whether to cross moral lines at Diana's request. Dan has figured out who is publishing his book, and seeks help to stop it, but he ends up in the spotlight anyway. Chuck helps Dan come to terms with his fate, just as Dan continues to try to help Chuck break through his emotional block. Serena and Charlie return to the Upper East Side from California.
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After much deliberation, Dan decides to gather Serena, Blair, Nate, Chuck, Rufus and Lily to reveal the truth about his book in the hope that they will support him at his book party. Meanwhile, Blair and Louis hit a crises point after Louis reads Dan's book. Diana learns incriminating information about one of Nate's friends and uses it to her advantage.
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In the midst of celebrating Yom Kippur with family and friends, Blair and Louis find themselves in a power struggle with Louis' family. Serena's boss puts Serena in the awkward position of choosing between her new job and her relationship with Dan. Diana prepares to debut the New York Spectator, but an unfortunate last-minute surprise delays the launch and Diana expects Nate to do whatever it takes to save the day.
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Blair makes all of her former minions and Charlie compete to secure the coveted bridesmaid spots in her upcoming royal wedding. Nate is tired of keeping his relationship with Diana secret, so he decides to use Charlie to make Diana jealous. Serena's boss is determined to acquire the film rights to Dan's book, so Serena must put her personal feelings about Dan and the book aside in order to close the deal.
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Several of our favorite Upper East Siders attend a performance of Punchdrunk's provocative theater experience, "Sleep No More," which translates to masks, anonymity and some surprising romantic twists by the end of the evening. Meanwhile, Diana sets her sights on Serena in her quest to ruin Gossip Girl. Dan is out on his book tour, but things aren't exactly as they appear to his friends and family.
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Serena is hard at work planning a dream bridal shower for Blair, but it should come as no surprise that Serena has to plant some false information about the shower in order to keep Blair from finding out all the details. Chuck and Dan decide to spend the day together to distract themselves from the fact that they didn't make the invite list for Blair's shower. Nate and Serena find a silver bullet in Diana's war against Gossip Girl, but struggle about whether to use it or not.
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Lily, Charlie and Serena eagerly anticipate the Studio 54 party being thrown in CeCe's honor. Nate takes on a new role at the Spectator, but his first big story turns out to be about someone he knows all too well.
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Lily throws Charlie a party to officially introduce her to New York society. Meanwhile, Charlie's ex-boyfriend, Max, throws a wrench into Charlie's future as an Upper East Side princess. Dan decides it may be time to tell Blair the truth about his feelings for her.
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Blair prepares to celebrate her upcoming royal wedding with a bachelorette party, but others scheme behind her back to make this a night to remember. After discovering the truth behind Chuck and Blair's car accident, Nate joins forces with a surprising ally to gather the evidence. Serena and Dan pretend to be dating again to protect someone close to them.
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The much-anticipated 100th episode will open with a musical dream sequence featuring Serena, Blair and all the men in their lives. Also, while Chuck wrestles with the reality that Blair is about to walk down the aisle with Prince Louis, the return of Georgina Sparks might make the royal affair a royal disaster.
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Blair must make a difficult decision about her future, the consequences of which could hurt those she loves most. Serena takes the blame for an incident with Gossip Girl in order to protect someone she loves. Georgina smells the scent of scandal and decides to follow its trail.
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It's Valentine's Day on the Upper East Side and Blair can't resist playing cupid for someone she loves. Georgina is intent on stirring up more drama, so she decides to crash Nate's Valentine's Day party. Meanwhile, Serena is shocked by something she witnesses at the party.
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Dan feels honored when he learns that Upright Citizen's Brigade is performing excerpts from his book, Inside. Blair tries to prove Serena's suspicions wrong in order to save their friendship. On her way out of town, Ivy ends up on a collision course with the van der Woodsens.
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Blair thinks Cyrus may have found a potential loophole in her prenup. Chuck and Georgina partner up in a scheme, but it has an unpredictable outcome. Meanwhile, a family crisis brings William van der Woodsen back to the Upper East Side.
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To celebrate their official coming out as a couple, Blair and Dan host a glamorous British-themed Salon, including guests Julian Tepper and Jenna Gribbon (founders of The Oracle Club). Lola lands the audition of a lifetime, but Gossip Girl may have other plans for the Upper East Side's latest It Girl. Meanwhile, Lily and Rufus disagree over the best way to handle the Ivy situation, and Serena and Diana face-off over secrets they both would prefer remain secrets.
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Blair feels like her Upper East Side status might be slipping away and devises a plan to assure that doesn't happen. Meanwhile, Lily throws a family gathering - including William, Carol and Lola - in an attempt to prove the van der Woodsen family is as united as ever. Finally, Nate digs into Diana's past and is surprised by what he discovers.
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Chuck, Nate, Blair, Serena and Lola team up to uncover what they think is an explosive secret between Diana and Jack. Meanwhile, Dan is offered a prestigious fellowship in Rome for the summer.
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When Gossip Girl goes after Blair as she's never done before, Serena admits she may have unintentionally played an important role in Blair's latest nightmare. Meanwhile, Nate invites Lola to move in with him, and Lily must make a big decision about the future of her marriage. Finally, by episode's end, Blair will make a choice between the two men in her life... will it be Chuck or will it be Dan?
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