1.sērija
"Yes, Then Zero"
While working as a production assistant in Hollywood, Serena makes a mistake while trying to impress her new boss (guest star Michael Michele). Chuck and Nate arrive in Los Angeles to visit Serena where Nate gets involved with a shady older woman (guest star Elizabeth Hurley) and Chuck has a meeting of minds with actress/stuntwoman Zoë Bell (playing herself) as he struggles to get over Blair. Meanwhile, Blair and Louis return to New York from Monaco after spending the summer planning their wedding. Louis' problem in supporting Blair's difficult choices and nearly impossible demands threatens their relationship when she begins to see him as weak. Also, Dan gets help from Louis in a desperate attempt to prevent his book from being published in a local magazine. It is revealed in this episode that Dorota is pregnant and expecting her second child. Towards the end of the episode, it is also hinted that Blair is the one that is pregnant in which Dorota lied for her. As she is fitted for her wedding dress, the dress fitter says that by the time of her wedding she will be showing. Also, Serena runs into Charlie in Los Angeles still unaware about her real identity, Ivy Dickens, whom has moved to California with her boyfriend, Max. 

2.sērija
"Beauty and the Feast"
Blair tries to conceal the news of her recent pregnancy from Louis as the arrival of her future sister-in-law Beatrice (guest star Roxane Mesquida) nears. Nate reconnects with the mysterious Diana Payne (guest star Elizabeth Hurley), a woman whom he had a fling with in Los Angeles who offers him a job opportunity to work at her publishing company, called Spectator, in New York. Meanwhile, Dan is desperately in need of help from Chuck to stop his novel from being published, but finds out that Chuck is hiding a secret. Ivy, still in character as Charlie, tries to avoid her real identity from an unsuspecting Serena but her plans affects her life in L.A. with her unsuspecting boyfriend Max. Blair's plan doesn't go accordingly; since Beatrice overhears her tell Dan that she's pregnant, not bulimic.

3.sērija
"The Jewel of Denial"
Serena and Charlie return to New York. Worrying that her identity will be revealed, Ivy decides to start making her own choice by being a part of New York's social society as Charlie. Meanwhile, Dan learns that his former mentor, Noah Shapiro, is responsible for publishing his novel. After his attempts at stopping Noah fail, Dan soon ends up in the spotlight. Chuck tries to break through his emotional block. Unknowingly, Nate is persuaded by the ruthless man-eater Diana (guest star Elizabeth Hurley) to cross moral lines while interviewing a couple at the Jenny Packham fashion show. Lily is finally released from house arrest and attends the fashion show with Rufus, despite the fact that her social life is in shambles. After learning that Ivy stole some of Charlie's trust fund money for herself, Carol Rhodes tracks down Ivy to New York where Ivy threatens to reveal their scam, as well as implicate Serena and the entire Van Der Woodsen family, if Carol does not back away. Elsewhere, a very reluctant Blair decides she does not want to learn who the father of her unborn child is, but is later seen telling Chuck that she is pregnant with Louis' baby, but adds "Part of me wished it was yours". He is both amazed and hurt. When Blair tells Louis that she is pregnant, he is estatic, but at the end Blair is seen hiding the test results in a drawer. Also, Nate finds Ivy's missing cell phone with her text messages from her boyfriend Max, but does not make the connection that Ivy and Charlie are one and the same.

4.sērija
"Memoirs of an Invisible Dan"
Dan is about to be announced as author of "Inside" so he gives a copy of the book to Blair, Serena, Nate, Chuck and Rufus hoping they will be supportive at his upcoming book party. In the book, Dan described Serena as the "old Serena": drinking, dating teachers, being shallow, partying, reckless, and having random sex. Nate doesn't receive a character description, but is joined with Eric (a younger, gay character with political relatives). Chuck is the only one in the book whom is described as he really is: lonely, cynical, without friends or families. The book talks about Blair and Dan having sex, and when Louis reads it he says he can't trust Blair anymore. Blair is afraid she will have to raise the baby on her own if he leaves and finally tells Serena. Louis apologizes for his behavior and agrees to trust Blair. Even Rufus becomes angry and alienated with Dan when he says he had never regretted leaving the music industry to have a family, until upon reading the book, which portrays him as marrying Lily just for money. Meanwhile, Diana makes the connection of Ivy and Charlie being the same person and forces Charlie to work for her at Spectator. Also, Serena's boss tells her to get the film rights for "Inside" and that she has only one week.

5.sērija
"The Fasting and the Furious"
Louis' mother Princess Sophie and his sister Beatrice pay another visit to New York where Blair announces her pregnancy to everyone. While her stepfather and mother, Cyrus and Eleanore, decide to throw a Yom Kippur dinner party to celebrate, Sophie and Beatrice try to get Blair to accept a series of conditions following the marriage. Blair naturally refuses, and Louis must choose between standing beside Blair or his mother. Meanwhile, Serena tries to get back into Dan's good graces after her boss tells her to ask Dan to gain the movie rights to his book. Charlie asks Nate for help after Diana gives her a difficult assignment to find more dirt on the Van der Woodsen family kept in the family safe. As Rufus and Lily continue to avoid talking with Dan over his book, Chuck connects with an attractive therapist who rebuffs his advances and seems to see right through his character for who he really is.

6.sērija
"I Am Number Nine"
Blair tries out three of her former minions for her Bridesmaids slots, and Charlie willingly teams up with the group in order to seek out a story where she proves herself to be more than a match for the Mean Girls. Nate becomes more frustrated that Diana refuses to publicly speak about their romance. So, Nate tries to make Diana jealous by asking Charlie to accompany him to Diana's party celebrating the opening of her new gossip Internet blog at Spectator. Meanwhile, Serena is forced by her boss, Jane, to secure the screenwriting rights for Dan's book, who quickly realizes that Jane wants someone else to write the screenplay in order to make the movie even more sordid and absurd as well as marketable. Also, Chuck discovers that his therapist, Dr. Eliza Barnes, has been recruited by Louis in order to dissuade Chuck from pursuing Blair any further.

7.sērija
"The Big Sleep No More"
Several of the group 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. Blair drags Dorota along with her as she sets out to prove that Chuck's attempts to reform himself into a better man is a scam. Meanwhile, Diana sets her sights to snag Serena a job at Spectator as part of her twisted quest to ruin Gossip Girl's website. When Charlie/Ivy's ex-boyfriend, Max, arrives in town to look for her, Diana sets about manipulating both of them, as well as Nate, hoping to cause a major confrontation for her own deranged enjoyment. Elsewhere, Dan sets out on his book tour, but Rufus and Lily discover that he isn't exactly having the experience as he claims to be. At the end, more shocking twists are revealed as the evil Diana and Nate's crooked grandfather, William van der Bilt, are revealed to have been working together to orchestrate Nate's employment with Diana as part of sinister grand plan for Nate, while Max, sent away by Diana on a ruse, accidentally discovers Ivy's double life of impersonating Serena's cousin Charlie.

8.sērija
"All the Pretty Sources"
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. Meanwhile, 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 when they uncover a list of all of Gossip Girl's contacts, but struggle about whether to use it or not. But when the list is leaked anyway, Nate and Serena accuse each other, then Nate accuses Diana, but Blair finds out that the culprit is Louis. Elsewhere, Max confronts Ivy about her double life of impersonating Charlie who tells him that Charlie is her real idenity. But Max quickly sees through Ivy's lies and instead of informing Lily or Serena or the authorities with what he knows, he instead blackmails Ivy for a large sum of money. Also, William van der Bilt makes his presence known where he forces Diana to quit as editor-in-chief of Spectator so that Nate can take her place. Chuck tells Dan that he is in love with Blair. The episode ends with Blair visiting Chuck at the Empire after she learns from Serena that Chuck really has changed.

9.sērija
"Rhodes to Perdition"
CeCe Rhodes arrives back in New York where Lily and Serena are planning to throw her a Studio 54 party in her honor. Serena continues dating Max who begins blackmailing Charlie. Meanwhile, Dan meets with his publicist Alessandra where they create a rival "dan fan" and "dan hater" accounts on twitter in order to create online buzz for his book. Blair attempts to figure out how to make Louis more like the "new" Chuck by spending the day with Chuck. She accompanies him to therapy and demands to know how he's improved himself only to find out that he's let her go. Upset she runs home and later reveals to Chuck that she's afraid she is the one that brings the dark side out in him and Louis. Chuck assures her that she is "the lightest thing that ever came into my life" and tells her he let her go because she asked him to. He just wants her to be happy. Also, Nate is the new boss of the Spectator and one of his employees finds out that his cousin Trip's wife, Maureen, might be having an affair. He soon figures out, however, that Maureen is faking an affair in order to create a sympathetic image for Trip in the public eye before the upcoming election. Serena learns about Ivy and Max and breaks up with him and Carol Rhodes visits to help find a cover story to get "Charlie" her trust fund and to help keep her there where she's loved. In the final confrontation, everyone believes Ivy's false story that she really is Charlie and pretended to be Ivy when she was with Max, even though he calls her a liar and says otherwise. Ivy also finds out that CeCe is sick, but keeps it a secret. The episode ends with Max reaffirming his threats to Ivy to expose her scam, Chuck telling Nate that he still loves Blair, and Blair looking despondent in her bedroom, refusing to talking to Louis who is out of the country.

10.sērija
"Riding in Town Cars with Boys"
Serena and Lily prepare Charlie for her first debutante ball to welcome her into New York high society, but the vindictive Max is determined to reveal Charlie/Ivy's secret by any means necessary. Meanwhile, Blair must choose where she stands with both Louis and Chuck as she hides out at the Humphrey loft in Brooklyn from the press. Dan realizes that it is time to tell Blair the truth about his feelings for her. Louis returns to New York where he meets with Serena and confides in her about his fears about his future with Blair. Nate learns that his grandfather, William van der Bilt, owns the majorty of stock shares at Spectator and he influenced Diana to hire him. William invites Nate to an upstate retreat, but Nate's cousin, Trip, has been excluded. After Dan sacrifices his own love for Blair for her happiness, Chuck and Blair are hurried into a car from Charlie's debutante ball. Their car is tailed by vicious paparazzi (Charlie sent a blast to Gossip Girl and tipped them off in order to keep them away from her) who cause them to crash, leaving Chuck fighting for his life and the pregnant Blair fighting to keep her baby. After Max's pleas to both Serena and Nate about Charlie's real identity fall on deaf ears, he has a run-in with Trip van der Bilt whom he apparently tells his story about Ivy. Charlie calls Carol Rhodes to tell her that she is leaving New York City after she tells Rufus that she is a fraud. Also, Diana is called by Jack Bass and informed about Chuck and Blair's car accident; she is somehow involved.

11.sērija
"The End of the Affair?"
Through a series of emotional flashbacks, Blair reveals to Serena what really happened in the aftermath of her tragic car accident with Chuck. Dan tries to help Blair recover, while both Chuck and Louis mistaken their bonding as an affair. Meanwhile, Nate discovers information about the accident that suggests possible foul play. Having successfully shut down Gossip Girl's website, Serena is reluctant to become the next Gossip Girl as her work at Spectator News takes off. Elsewhere, Lily is worried by Charlie's long absence and decides to hire a private detective to track her down despite Rufus' objections. Vera Wang makes a cameo as herself at Blair's dress fitting.

12.sērija
"Father and the Bride"
Blair decides to throw herself a bachelorette party, but shady enemies whom include Beatrice (guest star Roxane Mesquida), and her co-conspirator cousin Father Cavette, scheme to ruin and humiliate Blair, with an unknowing Chuck as their patsy, in order to prevent Blair's upcoming marriage by any means necessary. Meanwhile, Nate, with the distant assistance of Gossip Girl, finally discovers that Trip was responsible for the car accident that affected Blair and Chuck and he contacts William van der Trip for help to expose Trip's scheme. Also, Serena and Dan continue their fake relationship to protect Blair while Dan becomes uncertain about writing again.

13.sērija
"G.G."
Blair's wedding day finally arrives, along with a vengeful Georgina Sparks and her co-conspirator husband whom are determined to ruin Blair's wedding by any means necessary. Meanwhile, Serena decides that she has to tell Dan how she feels while Nate unknowingly meets the real Charlie Rhodes working as a waitress at the reception. Elsewhere, Chuck must decide whether or not to make a final grand gesture to show Blair how he feels until Blair's mother, Eleanor, approaches him to persuade him to stop the wedding. Blair's estranged father Harold, and her stepfather, Cyrus, try to get Blair to choose one of them to escort her down the aisle, while Louis' mother, Sophia, again tries to tell him that Blair is not, and never will, be trustworthy. The identity of Gossip Girl is reveleaed at the end of the episode to be Georgina Sparks.

14.sērija
"The Backup Dan"
Blair makes a huge decision about her future. Serena takes fault for an incident involving Gossip Girl. Georgina comes back.

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