In the wake of the Kiss on the Lips party, Serena receives a cold reception from Blair. Serena decides to take Dan to Chuck's fundraiser.
The Upper East Side teens of Constance Billiard and St. Jude's prepare for a visit from Ivy League representatives. Meanwhile, Blair discovers a shocking secret about Serena.
Blair's mother chooses her to be the new face of her clothing line. Serena and Dan are reminded that they come from two very different worlds. Nate and Chuck have a boys weekend.
Dan tries to impress Serena for their first official date. Jenny is invited to an infamous Blair Waldorf sleepover. Meanwhile, Lily finds out that Erik is missing from the treatment center.
Dan finds himself torn between two girls when his childhood friend returns to New York and declares her feelings for him. At the masked ball, Blair sends Nate on a scavenger hunt.
Serena and Dan finally accept that they are crazy about each other. Jenny discovers a secret that her parents have been keeping from her. Blair is once again devastated by Nate's actions.
Blair is feeling heartbroken and guilty by the current state of her relationship with Nate and her recent indiscretion, but she manages to put on a happy face for her 17th birthday party.
Dan invites Serena and her family to spend the holiday with his family, creating an uncomfortable situation for Rufus and Lily.
Serena's grandmother announces that Serena must go to Debutante Ball. A jealous Nate begins to suspect that Blair is seeing someone else. Jenny finds herself defying her parents.
Blair's father comes home for the holidays with an unexpected guest. Jenny and Vanessa help Serena get the best Christmas present ever for Dan, who has a surprise of his own for Serena.
Serena, Blair, Nate, Chuck and their class break into the school swimming pool for a night of fun, but when someone nearly drowns, the school threatens to expel the ones responsible for the break-in.
Gossip Girl has a special report that spreads like wildfire at Serena's expense. Meanwhile, Chuck and Nate fight over Blair and Dan struggles to reveal his feelings to Serena.
Having been dethroned as Queen Bee, Blair returns to school with the support of Serena. Meanwhile, Serena struggles to adjust to living with Chuck, and Jenny's drive to be popular hits an all time high.
Serena's world is turned upside down when her former friend returns to Manhattan. Nate finds romance with someone unexpected and Jenny meets a new guy who might be her ticket to permanent popularity. Meanwhile, Blair hatches a secret plan to sabotage her biggest rival.
Georgina informs Serena that she is prepared to reveal a secret from Serena's past. Blair and Jenny's power struggle continues when each of them start spreading scandalous rumors about each other on Gossip Girl.
After Georgina reveals the true reason Serena left Manhattan, Serena falls back into her old habits. Meanwhile, Rufus is excited when his band is invited to perform at a Rolling Stone-sponsored concert.
Blair takes matters into her own hands to help Serena with Georgina. Lily prepares for her wedding as it is designed to be the Upper East Side's social event of the year. Serena finally tells Dan the whole truth about her past.
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.
