Filmed entirely in New York and based on the popular series of young-adult novels by Cecily von Ziegesar, "Gossip Girl" revolves around the privileged prep school teens on Manhattan's Upper East Side and the anonymous blogger, Gossip Girl, who provides them with the latest rumors about their highly exclusive inner circle. In the series premiere, 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. Serena's best friend, Blair Waldorf, has conflicted feelings about her friend's return since she has enjoyed being the Queen Bee during Serena's absence and might not be ready to relinquish her new position on the social ladder, not to mention the fact that she has always suspected there may be unspoken feelings between Serena and her longtime boyfriend, Nate.
1.02 The Wild Brunch
There's nothing Gossip Girl likes more than a good cat fight!!! It's the day right after the Kiss on the lips party and Serena receives a cold reception from her former best friend Blair. Blair reveals that she knows that Serena and Nate slept together, before Serena mysteriously went to boarding school. Then Serena decides to take Dan to Chuck's fundraiser brunch at The Palace. Meanwhile little Jenny asks Blair for advice, and Blair realizes that she maybe gains something by allowing Jenny into her inner circle.
1.03 Poison Ivy
It's Ivy week for the Upper East Side teens of Constance Billiard and St. Judes and the visiting representatives arrival brings more than just college applications. Cutt-throat rivalry is at it's sharpest this week as the students compete for prestigious positions. Blair discovers a shocking but juicy secret about Serena and plots to drop the bomb at the best possible moment. Dan is sure that landing the coveted usher position with the Dartmouth rep will either make or break his future at the school. Unfortunately, it's Nate who nabs the position, despite total disinterest in the school. Meanwhile, Jenny gets close to Serena's younger brother Eric and Rufus asks Lily for a favor.
1.04 Bad News Blair
Fashion victim!!! Blair gets excited when her mother, Eleanor, chooses her to be the new face of her clothing line. However, Blair's happiness turns quickly into feelings of betrayal and jealousy when Serena takes her spotlight and Blair finds herself back in Serena's shadow. Meanwhile, Serena and Dan remember once again that they come from two very different worlds. Also, Nate and Chuck do a boys weekend to blow off steam after Ivy Week ends.
1.05 Dare Devil
It's their first official date and Dan tries to impress Serena with an elaborate plan for the date, but fails to understand that Serena is happier with beer than champagne. 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, Lily finds out that Erik is missing from the treatment center, and she finds herself seeking help from her ex-boyfriend, Rufus.
1.06 The Handmaiden's Tale
Masquerade Ball, anyone? Dan finds himself between two girls when his childhood friend, Vanessa, returns to NY and declares her feelings for him, just as he and Serena are trying to figure out what they mean to each other. At the masked ball, Blair sends Nate on a scavenger hunt, but Nate is distracted by his feelings for Serena. Although Blair said that outsiders were not welcome to the party, a disguised Jenny and Dan sneak into the ball. Finally, Lily asks Rufus to accompany her to an Eleanor Waldorf event only to make Bart Bass jealous.
1.07 Victor/Victrola
Things are heating up between Serena and Dan. Serena and Dan finally accept that they are crazy about each other, despite that they come from polar opposite worlds. Chuck thinks of investing in a club trying to make his father Bart Bass proud of him. Nate confronts his father, about the drugs he found in his house but he denies having a problem. Jenny discovers a secret that her parents have been keeping from her. Finally, Blair is devastated by Nate's actions when Jenny reveals that Nate kissed her by accident thinking she was Serena.
1.08 Seventeen Candles
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 and attempts to hide her feelings from her friends. Hoping that Serena and Vanessa can bond, Dan takes Vanessa to Blair's birthday party, but this ends up making Serena more uncomfortable. Jenny brings her mother home as a surprise, but Rufus isn't ready to forgive and forget. Finally, Nate's parents ask him to make a huge sacrifice to save his father's business as he faces charges of embezzlement and fraud.
1.09 Blair Waldorf Must Pie!
Dan invites Serena and her family to spend the holiday with his family, creating an uncomfortable situation for Rufus and Lily. The children are unaware of their complicated romantic past. Meanwhile, Blair's freaks out when she learns that her father isn't coming home for Thanksgiving. Nate spends the holiday with his family, but their awkward dinner quickly goes from bad to worse.
1.10 Hi, Society
Serena had no intention of attending the upcoming Debutante Ball, until her grandmother, CeCe, announces that she has to. But, Dan is not what CeCe wants as an escort for Serena, and she makes her opinion heard loud and clear, causing a riff between Serena and Dan. Although they are officially broken up, Nate asks Blair to go to the ball with him. She accepts but only as friends. Then a jealous Nate begins to suspect that Blair is seeing someone else. Jenny finds herself with the decision of either attending her mother's art opening or following her dreams to the Debutante Ball, even though her parents don't want her to go.
1.11 Roman Holiday
Blair's father, Harold, comes home for the holidays with an unexpected guest, his boyfriend, Roman. Blair cannot hide her disappointment and makes a plan to get rid of Roman for ever. Jenny and Vanessa help Serena get the best Christmas present ever for Dan, who has a surprise of his own for Serena. Then when Chuck texts Blair that Nate is with him in Monaco, Blair worries that Chuck may tell Nate about their hook-up. Rufus refuses to remain the understanding husband any longer after Alison's former lover calls the house.
1.12 School Lies
Impromptu party at the school swimming pool!!! Serena, Blair, Nate, Chuck and their class break into the school swimming pool for a night of fun, but when someone nearly dies, the school threatens to expel the person responsible for the break-in. Everyone agrees to not say anything, but this creates major problems between Serena and Dan, because Dan is not ready to take the fall for someone else and risk his future. Vanessa while working on a documentary project about private schools, accidentally captures Blair and Chuck discussing their affair. Lily tries to tell Rufus how she really feels about him.
1.13 The Thin Line Between Chuck and Nate
Gossip Girl reports that Serena van der Woodsen was seen buying pregnancy tests. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip. Nate finds out about Blair and Chuck's affair. Everyone else also finds out what happened and Blair's life comes crashing down. Dan struggles to tell Serena those three words.
1.14 The Blair Bitch Project
Having been recently dethroned as Queen Bee, Blair returns to school with the support of her BFF, Serena to find she is still on the outs with her old friends. Dan visits his mother over Spring Break, and when he returns Jenny is on the verge of becoming a full-fledged member of the A-List crowd. Jenny must go to dangerous and even illegal lengths to fit in. Serena struggles to adjust to living with Chuck, and receives disturbing packages from an unknown sender.
1.15 Desperately Seeking Serena
Serena's world becomes a chaos when a former friend the evil Georgina Sparks returns to town. Dan sees Serena preoccupied and he assumes that it has something to do with Chuck, her soon step-brother. Nate connects with the last person he expected, Vanessa.
Hazel and Penelope try to recruit Nelly Yuki to be part of their club but it is not easy. Blair supervises the whole operation and hatches a plan to sabotage her biggest rival, Nelly Yuki. When Nelly breaks down after being reminded of her recent break-up with her boyfriend, the ladies find their way in and Nelly comes to the Waldorf penthouse. Then Blair invites the boyfriend over.
Meanwhile Serena goes out with Georgina but things get so bad that Serena thinks someone spiked her drink. Jenny develops a crush on 16-year-old dog-walker, Asher Hornsby, who might be her ticket to permanent popularity.
1.16 All About My Brother
Georgina informs Serena that she can reveal a deep dark secret from Serena's past, but no one is prepared for what Georgina does next. Blair and Jenny's power struggle continues when each of them start spreading scandalous rumors about each other on Gossip Girl. Dan sees Jenny's new beau Asher cheating on her, but Jenny doesn't believe him. Rufus goes to Lily for advice on how to handle Jenny's new behavior. Serena tries to confront Georgina but she leaves before Serena had a chance. After this Serena says that she and Georgina are not friends.