Gossip Girl is busy spreading the news that "it girl" Serena Van Der Woodsen has returned to Manhattan after a mysterious and self-imposed exile to boarding school.
In the wake of the scandalous Kiss on the Lips party, Serena receives an icy cold reception from her best friend Blair, who reveals that she knows Serena slept with her boyfriend, Nate, before mysteriously running off to boarding school.
The Upper East Side teens from Constance Billard and St. Jude's prepare for a much-anticipated visit from the Ivy League representatives. Blair uncovers a scandalous secret about Serena that may not remain a secret much longer.
Blair’s mother, Eleanor, chooses her to be the new face of her clothing line. However, Blair's happiness soon turns to 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 to blow off steam after Ivy Week.
Dan makes elaborate plans to impress Serena on their first official date. The 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.
Dan and Serena are trying to figure out what they mean to each other when Vanessa, Dan’s childhood crush, returns home and declares her feelings for him.
Serena and Dan's relationship is blossoming, and it appears it's about to become physical. Chuck contemplates investing in a burlesque club in the hopes of making his hard-to-please father, Bart, proud of him.
Devastated by the current state of her relationship with Nate and still dealing with the guilt from her recent indiscretion with Chuck, Blair puts on a happy face for her 17th birthday party and attempts to hide the truth from her friends.
While preparing Thanksgiving dinner, Serena tells Blair that she saw Chuck and Blair together. Blair admits to having slept with Chuck twice, and gets defensive and angry when Serena expresses concern.
Serena has absolutely no intention of attending the upcoming Debutante Ball, until her manipulative grandmother, CeCe, announces that she won't take no for an answer.
When Blair's father, Harold, comes home for the holidays with an unexpected guest -- his boyfriend, Roman -- Blair finds it difficult to hide her disappointment and tries to break them up by inviting Roman's old boyfriend to their Christmas party.
Serena, Blair, Nate, Chuck and their entourage break into the school swimming pool for a night of fun, but when a member of their group nearly drowns, the school threatens to expel the person responsible for the break-in.
There are rumors around school that Serena is pregnant, but what Gossip Girl didn't know when she printed photos of Serena buying pregnancy tests is that she was buying them for Blair, and that Blair isn't even sure whether Nate or Chuck is the (potential) father.
Having been recently dethroned as Queen Bee in the last episode by Gossip Girl, with an assist from scheming "little J", Blair hesitantly returns to school with the support of her BFF, Serena.
Serena's Upper East Side world is turned upside down when her former partner in all things bad, Georgina Sparks, returns to Manhattan to stir up trouble and Serena's past.
Georgina informs Serena that she is prepared to reveal damaging information from Serena's past, but no one is prepared for what Georgina does next. Blair and Jenny escalate their popularity war by spreading scandalous rumors about each other through Gossip Girl.
As a result of Georgina revealing the true reason that Serena fled Manhattan for boarding school, Serena falls back into her old habits and Blair, Nate and Chuck must put their complicated feelings for each other aside to help their friend.
With her best friend Serena's life and reputation on the line, Blair decides to take matters into her own hands in dealing with the manipulative and evil Georgina Sparks. With Rufus never far from her thoughts, Lily prepares for her wedding day which is destined to be the Upper East Side's social event of the year. Serena finally pours out her heart and the truth about her past to Dan.