Blair has spent a fabulous summer in Paris without realizing her former love, Chuck Bass, has been shot. As much as Blair tries to distract herself from the pain Chuck caused her, his mysterious appearance in Paris with a beautiful new woman will force both of them to face what happened. Meanwhile, a newly single Serena has been enjoying a Parisian summer of love with boys, Blair and Balenciaga as she tries to avoid the inevitable decision about which of her two long-time beaus, Dan or Nate, she should return to. Back on the Upper East Side, Nate meets an intriguing girl, Juliet, who helps him realize that his summer of sexual conquests with the help of Chuck’s little black book was his way of avoiding his unresolved feelings for Serena. Meanwhile, Dan’s baby mama drama continues with Georgina. Finally, the van der Woodsen apartment is buzzing with activity as the “Fashion’s Night Out” event is planned.
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.
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.
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.
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.
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.
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.
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.
Chuck, Serena, Blair, Dan, Jenny and Eric find themselves faced with a crisis when a member of one of their families is hospitalized. Meanwhile, Nate attempts to help his parents, The Captain and Anne, put their complicated past behind them and reconcile.
Blair and Dan decide to team up to take down an MIA Juliet. The odd couple takes a road trip to Cornwell, where they find Damien Daalgard. He gives Blair and Dan some missing pieces to find out why Juliet is after Serena. Meanwhile, Juliet finds out about Blair and Dan's present in her home town and decides to return to New York to finish what she started. Lily is keeping a secret from Chuck, which Rufus finds out. Nate tells his mother about what the Captain has been up to and she decides to get through with the divorce. When Nate realizes he had it all wrong a last attempt to rescue his parent's marriage fails due to Anne's longing to the rich society of Manhattan.
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.
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.
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.”
With Russell Thorpe poised for a takeover attempt of Bass Industries, Chuck makes one last-ditch effort to save his family’s company. Blair is given a challenging assignment at W Magazine with the promise of a possible promotion. Serena struggles with her feelings for Ben.
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.
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. Billy Baldwin returns as William van der Woodsen, Lily’s ex-husband and Serena and Eric’s father.
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.
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.
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.
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.
The episode continues from the early events of the Constance Alumni event. Georgina Sparks turns up at the event looking for trouble. Serena and Vanessa reluctantly join forces to find Dan and Charlie, who does not take Dan's rejection of her well. Blair must make a choice between the men in her life when her life is in danger from Russell.
After a brief encounter abroad, Chuck and Blair make a promise to each other about their relationship, which leaves them once again apart. Dan, with some help from an unlikely ally, Georgina, is writing a scathing tell-all book that can only mean trouble. As the sole head of The Spectator, Nate is making his own decisions and is ready to go up against Gossip Girl. As word spreads that Serena is missing, the gang bands together to find her and are shocked by what they find.
Trying to prove herself in adult society, Serena hosts the Central Park Conservancy’s big gala, of which she is now the newest Board Member, and she and Nate both learn something shocking about their significant others. Blair prepares to debut her new fashion line, but a rival from her past holds the key to her future. With the help of Georgina, Dan lands some meetings with publishers, but he must decide if he is willing to sacrifice his integrity in order to get his work published. Meanwhile, Chuck tries to persuade Amira to help him look into his father’s past, even if it means jeopardizing Lily and Bart’s relationship.
Feeling the pressure to make her first Waldorf Designs fashion show a success, Blair must rely on help from an unlikely source, but some unexpected scheming causes a scandal on the runway. Serena discovers that befriending Steven’s daughter Sage is trickier than she thought, especially when she is forced to put her issues with Blair aside to make Sage happy. Nate publishes Dan’s first serialized article causing a stir and producing a serious threat. Meanwhile, Chuck begins to look into the clue that Amira left behind, which may help uncover what Bart is hiding.
Chuck’s continued investigation into his father’s dealings leads him to an unlikely event with Manhattan’s elite, where he hopes to find the one person who can tell him the truth about Bart. Serena and Steven decide to reveal their romantic histories so they aren’t surprised by anything, but neither was prepared for what they uncovered. With The Spectator in jeopardy after Dan decided to publish elsewhere, Nate must make a difficult decision to keep it in business. Meanwhile, Georgina pushes Dan to choose a worthy person to date to boost his image, but he finds himself drawn in a different direction.
After Eleanor gives Blair an ultimatum, Blair is even more determined to remedy Waldorf Designs’ problems by making a splash with a dress at the upcoming Cotillion, but a shocking revelation at the ball affects everyone. Serena becomes worried about Steven’s attitude toward her, but after some investigating she discovers the surprising reason why. Chuck finds an unlikely ally as he tries to drive a wedge between Bart and Lily’s relationship to help expose his father’s secret. Meanwhile, Dan publishes another article, but the effect is just the opposite of what he was hoping for.
Blair gets ready for her mothers imminent arrival, but is unprepared for the set of demands her mother puts upon her. Serena volunteers to help Dan find a new place to live, but their time together brings up unexpected emotions. With Ivy’s help, Chuck discovers there is evidence incriminating his father in illegal activities and enlists the help of Nate to retrieve it. Meanwhile, Rufus and Ivy are excited about their art gallery opening until they find an empty RSVP list and must scramble to find another way to make the event a success.
Serena and Dan realize that they need to make amends with the people they have wronged. Blair has one last chance to prove to her mother her worth as a fashion designer and with Serena’s help, comes up with a plan to make her line the “it” look for Sage and her friends. Chuck is close to getting the evidence he needs against his father, until one of his closest allies reveals his plan to Bart.
Serena and Dan decide to throw their first Thanksgiving together, inviting only their closest friends, but everyone seems to have their own agenda for attending. Feeling defeated by his father, Chuck begins a downward spiral, leaving Blair to find a solution to his problems. Meanwhile, Dan has written his latest exposé, but he must make a tough decision whether to publish it, knowing it could destroy a close friendship.
After a run-in with an increasingly paranoid Bart, Blair grows alarmingly concerned for Chuck’s safety. However, feeling confident that his father will never hurt him, Chuck makes a deal that could change his life. Wanting to make things better for Chuck, Blair devises a plan with the help of Serena, Georgina and Sage to try and get what they need out of Bart. Meanwhile, Nate's financial dilemma finally lands him in a place that he never thought he would be.
In a fashionable farewell to remember, our favorite Upper East Siders join forces for one last soiree, and the shocking identity of Gossip Girl is finally revealed.
Vanessa uses the scandalous picture of Catherine and Marcus to blackmail Blair into being a nicer person, so Blair seeks revenge by enticing Chuck to seduce Vanessa. Lily and Bart throw an extravagant housewarming party and expect their children to make them proud in front of the attending press, but a rebellious Serena isn't ready to play by their rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.
Jenny befriends a young model, Agnes, who encourages Jenny to not only explore her wild side, but also confront her boss, Eleanor Waldorf, who is attempting to "borrow" Jenny's designs. Serena meets an artist, Aaron Rose, and realizes they have an instant chemistry. Blair attempts to seduce Chuck, but it proves tougher than she ever imagined.
Serena invites Aaron to a charity event, but soon uncovers a secret Aaron has been keeping from her. Thinking it will help her get into Yale, Blair agrees to babysit the 15-year-old daughter of a Yale donor, but her plan quickly backfires. Meanwhile, Jenny and Agnes plan a fashion show.
Blair sets out on a mission to break up her mother and Cyrus Rose, her new man. Jenny moves in with Agnes as the two continue with their plans for their own fashion line. As Serena continues to fall for Aaron, she learns something that may derail their relationship forever while Dan interviews Bart Bass for an article for New York Magazine.
It's Thanksgiving time and Blair is offended when her Mom's new man hijacks her Thanksgiving traditions. Lily attempts to strengthen the frail bond between Rufus and Jenny. Eric discovers a secret about Bart. Vanessa and Chuck help Nate deal with his father.
As the annual Snowflake Ball approaches, Blair and Chuck make a bet that they can find the perfect date for one another. Aaron's ex-girlfriend, Lexi, becomes attracted to Dan, creating mixed feelings for Serena.
The entire Upper East Side of Manhattan is rocked when Bart Bass dies suddenly in a limo accident. Serena and Eric take the news very calmly while Lily has a troubling time despite her mother, Cece's, awkward attempts to comfort her. Chuck begins to blame Lily for his father's death and threatens to reveal a secret that Bart found on her before his accident. Meanwhile, Blair's mother, Eleanor, prepares for her latest marriage to Aaron's father Cyrus.
Because Chuck is MIA since his father's funeral, his Uncle Jack arrives on the Upper East Side to find and help him. Trying to forget her last conversation with Chuck, Blair focuses on being accepted into the most prestigious ladies club in the city, Colony Club. Jenny returns to Constance Billard and immediately takes on Penelope and her posse of mean girls, but no one is going down without a valiant Gossip Girl-worthy fight.
Chuck, Jack and Lily come together for the reading of the will which reveals what will come of the Bass empire. Rufus and Lily's relationship is put on hold as Rufus searches for the child he never knew he had. Meanwhile, Dan does some digging of his own and uncovers Rufus and Lily's secret, putting him in an awkward position.
The students are stressed out as they find out who was accepted and who didn't make the cut for early admission to Yale. Meanwhile, Serena bonds with Rachel, her Shakespeare teacher, who is unaware of what Blair has in store for her following receiving her first B. Chuck finds an unlikely ally in his feud with Jack and Nate and Vanessa have a romantic evening together.
Blair comes up with a devious plan to take down her new teacher, Rachel. Chuck has no recollection of what happened to him when he wakes up in a hotel. Nate and Vanessa try to help Chuck fill in the missing pieces of his night. Meanwhile Dan and Serena try to keep their relationship together as Rufus and Lily grow even closer.
The Constance Billard and St. Jude seniors have the production of "The Age of Innocence." Serena has a crush on the play's director, Julian, and enlists Vanessa's knowledge of theater to help her get the guy's attention. Blair receives bad news about her future that leads her on a witch-hunt for the person responsible. Dan and Rachel agree to stay away from each other in the aftermath of being discovered as more than teacher and student, but find it impossible to keep that promise. Chuck finds help in an unlikely friend, Carter Baizen.
Devastated by the turn her life has taken, Blair opts for a wild lifestyle instead of her perfect Waldorf life, causing Chuck and Serena to become concerned. Vanessa tries to convince Nate that he needs to move on after his mother's family, the Vanderbilts, abandoned him and his mother. Trying to be honest with each other, Lily and Rufus both put together their lists of past relationships.
Serena throws Jenny a sixteenth birthday party, but things spin out of control when Poppy Lifton turns the party into the social event of the season. Vanessa agrees to help Chuck in a plan concerning Blair and Nate. Meanwhile, Rufus searches for a way to cover Dan's tuition when he learns he will not receive financial aid to go to Yale.
Serena returns from her trip to Spain with Poppy and Gabriel. Blair makes a secret deal with Nate's grandfather. Dan takes a job to earn money for college.
Georgina returns to the Upper East Side but it's not the same Georgina we all knew, she's changed. Chuck and Nate's relationship is at a crossroads because of their mutual interest in Blair. Serena's relationship with Gabriel gets more complicated.
Blair puts pressure on Georgina to making amends for her past bad behavior by helping her in an evil plan. The rivalry between Nate and Chuck over Blair reaches a boiling point. Lily makes a secret plan to help Rufus with Dan's college tuition.
In a flashback to the 80s, 17-year-old Lily Rhodes gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her parents, Rick and Cece, and sister, Carol. Back in present day, Blair and Nate attend prom together, but the evening doesn't turn out exactly as planned and Chuck and Serena have a little something to do with that. Serena and Lily don't see eye-to-eye over Serena's recent run-in with the law. No Doubt performs in the flashbacks as an 80s band called "Snowed Out."
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 challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year. Lily and Rufus struggle to repair their relationship after Lily’s betrayal. As for the cliffhangers, Blair and Chuck finally… and Serena is shocked by… and Georgina decides to… and Dan, Nate, and Vanessa unknowingly…. Jenny and Eric do something they might end up regretting.
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.
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.
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.
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.
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.
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 a 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.
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.
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.
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. Blair turns to an unlikely person for help.
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.
Blair's flashbacks reveal the fallout of her and Chuck's car accident, which Nate realizes may have been caused by foul play. Meanwhile, Lily gets a private eye to locate Charlie; and Vera Wang makes an appearance at Blair's bridal-dress fitting.
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.
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.
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.
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.
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.
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.
Chuck invites Jack to town to thank him for saving his life, but finds the trip doesn’t go exactly as planned. Blair and Dan attempt to consummate their new relationship -- but unexpected roadblocks get in their way. Meanwhile, Ivy finds an unlikely ally in William in her quest to be accepted on the Upper East Side, and Nate is hopeful a new investor will save his newspaper.
Serena decides she is ready to relinquish the spotlight and sets out to make a reluctant Lola the next “It Girl” of the Upper East Side, starting with modeling at a Kiki de Montparnasse lingerie show. Meanwhile, Chuck reaches out to Blair or advice about his past, and Diana Payne’s return to The Spectator starts a power struggle with Nate.
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 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.
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.
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.
Blair enlists Serena to be her stand-in at an important meeting when Blair finds herself needing to be in two places at the same time. Meanwhile, Ivy and Lola team up to help Chuck with a personal vendetta, and Nate makes a decision about the future with Diana Payne.
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?
As summer draws to an end, Blair and Chuck continue to adjust to being in a relationship with one another. Serena returns from Europe with new secrets to hide and a new relationship with Carter Baizen. Nate also returns from vacationing and brings home a mysterious girl, Bree Buckley. Meanwhile, Rufus, Dan and Jenny spend the summer in the Hamptons and learn to adjust to the van der Woodsen's glamorous lifestyle
Blair, determined to have her Queen status at college, starts her first day at NYU along with Dan and Vanessa. However, Georgina, who was assigned as Blair's roommate, sets out to ensure that she does not retain her title. Serena gets ready to move into her dorm at Brown, but has a fight with Chuck before hand. This leads her to search out Chuck's enemy, Carter, to help her get even with him. Meanwhile, Nate and Bree's relationship continues to grow despite the tension their relationship could cause between their families.
Blair and Chuck face-off when the both set their sights on an item up for bid at Sotheby's. Serena begins to think that Carter may have returned to his old habits, Georgina becomes interested in Dan, and Vanessa thinks that something is wrong with Scott.
During the first day of school at Constance Billard, Jenny takes her place as the new Queen Bee. However, Blair gets in her way. Lily returns home to find that things are not as they were when she left them with Rufus. At NYU, Olivia Burke, an actress, enrolls and is assigned to be Vanessa's roommate.
Lily and Rufus decide to move up their wedding to the next day, but will someone or something come between them before they become man and wife? Chuck discovers a secret that Carter has been keeping from Serena. Dan and Vanessa are pulled into one of Georgina’s schemes. Blair is suspect of Bree and shares her concerns with Nate.
Vanessa, hoping to finally win her mother Gabriela’s approval, desperately vies with Blair for the honor of delivering the freshman toast at NYU, but at what price? Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple. Serena and Nate team up to help Carter Baizen.
Olivia says something she regrets during her appearance on Jimmy Fallon’s talkshow and tries to keep Dan from finding out. With election day around the corner, Nate suspects his grandfather will stop at nothing to get 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.
Not satisfied with just being Queen of Constance Billard, Jenny sets her sights on becoming the Queen of all the Upper East Side by landing the hottest escort for Cotillion. Meanwhile Dan and Vanessa try to convince Olivia to stay in NY by showing her the "true college experience."
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. 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.
On the anniversary of Bart Bass’ death, Chuck wrestles with an issue from the past and a serious car accident rocks the Upper East Side. Dan and Vanessa attempt to navigate their newly complicated friendship. When Jenny is accused of beating up one of her classmates, Eric is faced with a tough dilemma.
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.
Rufus and Lily grow suspect of Jenny’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.
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 it'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.
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 Eleanor’s fashion show, but the opportunity takes a big turn for the worse when Jenny learns that Agnes will be one of the models.
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 Serenas’s efforts. Dan and Vanessa’s new relationship hits a bump in the road.
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 she’s secretly meeting up with Carter Baizen. Rufus discovers that Lily has been lying to him about her whereabouts.
When Lily’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 didn’t get accepted into the Tisch writing program and Vanessa admits she may have been somewhat responsible.
Will's return to the Upper East Side continues to stir up problems for Serena, Lily and his long-standing rival, Rufus. Serena and Jenny's relationship is strained as a result of Jenny'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.
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.
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.