Season 1, Episode 1: Pilot
At a privileged prep school for teens on Manhattan's Upper East Side, the students first learn that Serena van der Woodsen is back in town the way they learn all the important news in their lives: from the Internet blog of the all-knowing, albeit, ultra-secretive 'Gossip Girl'. No one knows Gossip Girl's identity, but everyone in this exclusive and complicated vicious circle relies on her website and text messages for the latest scoop. Even Serena's closest friend, Blair Waldorf, is surprised to find that Serena has suddenly ended her self-imposed exile from a boarding school in New England and returned to Manhattan for school. Once the Upper East Side's most notorious party girl, Serena's reasons for returning are mysterious, although they may have something to do with her younger brother Eric, who's secretly in the hospital following a suicide attempt which is kept under wraps by their overprotective mother Lily. Whatever the reasons, the change in Serena is obvious, especially to Blair, whose friendship with Serena has always been competitive and difficult. Into this crowd comes Dan Humphrey, a kid from Brooklyn and whose freshman sister, Jenny, tries a little too hard to fit into Blair's circle of gossip friends, whom include 'Gossip Girl's contacts, Isabel and Kati. Blair's nice-guy boyfriend, Nate Archibald, is also troubled by Serena's return for his best friend, Chuck Bass, the school's snobbish cynic and resident bad boy, knows about a fling that Serena and Nate had which is why Serena left town to avoid a scandal which, in the snobbish world of high society, is social suicide. Elsewhere, Dan and Jenny's father, Rufus, a former rock musician and art gallery operator, also has a return of feelings for Serena and Eric's mother, Lily.
At a privileged prep school for teens on Manhattan's Upper East Side, the students first learn that Serena van der Woodsen is back in town the way they learn all the important news in their lives: from the Internet blog of the all-knowing, albeit, ultra-secretive 'Gossip Girl'. No one knows Gossip Girl's identity, but everyone in this exclusive and complicated vicious circle relies on her website and text messages for the latest scoop. Even Serena's closest friend, Blair Waldorf, is surprised to find that Serena has suddenly ended her self-imposed exile from a boarding school in New England and returned to Manhattan for school. Once the Upper East Side's most notorious party girl, Serena's reasons for returning are mysterious, although they may have something to do with her younger brother Eric, who's secretly in the hospital following a suicide attempt which is kept under wraps by their overprotective mother Lily. Whatever the reasons, the change in Serena is obvious, especially to Blair, whose friendship with Serena has always been competitive and difficult. Into this crowd comes Dan Humphrey, a kid from Brooklyn and whose freshman sister, Jenny, tries a little too hard to fit into Blair's circle of gossip friends, whom include 'Gossip Girl's contacts, Isabel and Kati. Blair's nice-guy boyfriend, Nate Archibald, is also troubled by Serena's return for his best friend, Chuck Bass, the school's snobbish cynic and resident bad boy, knows about a fling that Serena and Nate had which is why Serena left town to avoid a scandal which, in the snobbish world of high society, is social suicide. Elsewhere, Dan and Jenny's father, Rufus, a former rock musician and art gallery operator, also has a return of feelings for Serena and Eric's mother, Lily.
Season 1, Episode 2: The Wild Brunch
Serena confides in Blair that she had sex with her boyfriend, Nate, right before she skipped town. But Blair, being the person she is, vows a cruel revenge against Serina who decides that Dan would make a good escort for the fund raiser brunch at the Palace Hotel... a brunch hosted by none other than Jenny's would-be rapist, Chuck, and his uptight father Bart. Meanwhile, 'Gossip Girl' posts on her web bloc that Jenny, the eager freshman, paid a visit to ultra-cool Blair, who quickly realizes that granting the eager wannabe access to her elite inner circle might just prove useful. Elsewhere, Lily meets with Rufus about how their lives went since they parted 15 years earlier, and Dan discovers Lily's relationship with Bart, while Blair sends him running after she tells him all about Serina's sordid past.
Season 1, Episode 3: Poison Ivy
'Gossip Girl' narrates Ivy League week as the teens on the Upper East Side schools of Constance Billard for Girls, and the rival St. Jude's for Boys, prepare for a much-anticipated visit from the Ivy League representatives. The twisted and vindictive Blair, with Chuck's help, uncovers a scandalous secret about Serena that may not remain a secret much longer which involves Eric whom is still hold-ed up in the sanatorium. Dan has his heart and future set on the coveted usher position for the Dartmouth rep, only to be beat out by Nate who has no interest in the school despite pressure from his controlling father, The Captain. Meanwhile, Jenny bonds with Serena's younger brother, Eric, who confides in her about his depression and recent suicide attempt, while Rufus must swallow his pride and ask Lily for a favor to help Dan with a Dartmouth referral.
Season 1, Episode 4: Bad News Blair
Blair is thrilled when her mother, Eleanor, chooses her to be the new face of her clothing line. However, Blair's happiness soon turns to her typical 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 with the former trust-fund case, Carter Baizen, to blow off steam after Ivy Week, and who gets the guys into trouble with some of his poker player thugs. Elsewhere, Rufus bonds with an attractive art collector, named Bex, whom is interested in his latest painting at the Bedford Avenue Art Gallery where he works.
Season 1, Episode 5: Dare Devil
Dan makes elaborate plans to impress Serena on their first official date. 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, when Lily discovers that Eric is missing from his treatment center, she finds herself seeking help from her ex-boyfriend, Rufus
Season 1, Episode 6: The Handmaiden's Tale
Dan is torn between two girls when his childhood friend, Vanessa, returns home and declares her feelings for him, just as he and Serena are trying to figure out what they mean to each other. At the infamous masked ball, Blair sends Nate on a scavenger hunt, but Nate is ultimately still distracted by his feelings for Serena. Although Blair makes it perfectly clear that outsiders are not welcome, a disguised Jenny and Dan sneak into the ball. Elsewhere, Lily asks Rufus to accompany her to an Eleanor Waldorf event in order to make Bart Bass jealous
Season 1, Episode 7: Victor/Victrola
Things heat up between Serena and Dan when they admit they are in love with each other, despite that they come from polar opposite worlds (she from wealthy Upper East Side Manhattan, and he from working class Brooklyn). But Serena and Dan's plans to be alone to consummate their romance is interrupted by Vanessa who shows up wanting to spend time with Dan. Meanwhile, Chuck thinks of investing in a strip nightclub to make his father, Bart Bass, proud of him. Jenny discovers a secret that her parents have been keeping from her. Also, Blair is devastated by Nate's actions when Jenny reveals to Blair that Nate kissed her by accident at the masked ball the night before after he mistook her for Serena. Blair, (being the cynical b*tch she is), tells Jenny they are no longer friends. Nate's parents think that he should tell Blair he wants to marry her, even though he doesn't have strong feelings for her. The Archibalds and Waldorf's have a dinner party celebrating their new business deal together and it's obvious that Blair is giving Nate the silent treatment. Nate confronts his father about the drugs he found in his house, but he denies having a problem. The two get into a brawl and Nate's father punches him and as a result Nate turns his own father into the police. Afterwards, Nate gets ready to go see Chuck at the strip club he opened, but Blair stops him and tells him he needs to be with his father. Blair tells Nate that she doesn't need him and they break up and she heads over to the strip club saying she wants to "escape", which leads to a sordid tryst between Blair and Chuck in the backseat of his limousine.
Season 1, Episode 8: Seventeen Candles
Blair is devastated by the current state of her relationship with Nate and the guilt from 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 to ease the tension between Serena and Vanessa, Dan takes Vanessa to Blair's party so the girls can bond together, but this ends up making Serena more uncomfortable. Jenny brings her mother, Alison Humphrey, home as a surprise visit. But Rufus isn't ready to forgive and forget Alison for walking out on their marriage to find herself and concentrate on her artist work. Also, Nate's parents ask him to make a huge sacrifice to save his father's business as he faces charges of embezzlement and fraud.
Season 1, Episode 9: Blair Waldorf Must Pie!
Although it is Thanksgiving, hardly anyone has the holiday spirit. Blair and Serena have a fight once Serena admits that she saw Blair with Chuck, and Blair orders Serena to keep it to herself. Meanwhile, Nate and his family share a strained Thanksgiving meal before Mr. Archibald ends up in the hospital after a suicide attempt. Having been uninvited by Blair to the Waldorf Thanksgiving meal, the Van der Woodson family has dinner with the Humphreys at their loft in Brooklyn, and the tension between Lily, Allison, and Rufus is palpable. Back in Manhattan in the Waldorf penthouse, Blair revisits her bout of bulimia after discovering that her mother forbade her father to join them for Thanksgiving. Throughout the entire episode, there are flashbacks of last year's Thanksgiving involving how Dan met an stoned Serena for the first time as well as Blair's Thanksgiving with her father and mother before their seperation. There is a stark contrast between its joy and the present's strife.
Season 1, Episode 10: Hi, Society
As 'Gossip Girl' posts news of the annual Cotillion Ball to take place on the approaching weekend, Blair decides not to go with Nate, but she finds herself being featured in The New York Times and is enjoying her secret affair with Chuck. Serena decides not to go either, so her grandmother, CeCe, shows up to change her mind. Meanwhile, Jenny volunteers for the ball and Lily takes her under her wing. But the night of The Cotillion is the night of Alison's first art opening, and Rufus and Alison tell Jenny that she cannot attend the ball. Jenny decides to defy them both by secretly attending the dance anyway. Refreshed by Blair's newly buoyant attitude, Nate asks her to the Cotillion and she accepts, which makes Chuck jealous. CeCe tells Lily and Serena that she is sick with lung cancer and her last dying wish is to see Serena go to the ball, and she wants Serena to go with the wealthy Carter Baizen. The snobbish CeCe takes an instant dislike to Dan and she approaches Rufus with an offer pay him to convince Dan not to go with Serena. Dan learns of this and tells Serena that he does not think very highly of CeCe by telling Serena about how CeCe tried to bribe his father to persuade him not to attend. Surprisingly, the skeptic Serena refuses to believe Dan that her compassionate grandmother is a crafty snob, and she ends up going to the ball with Carter... both her and Dan having fallen right into CeCe's ploy. Also, Chuck manipulates Nate into thinking Carter is having an affair with Blair to provoke a fight with him.
Season 1, Episode 11: Roman Holiday
Blair's estranged father, Harold, comes home for the Christmas holidays with an unexpected guest: his gay lover Roman. Both Blair and her mother, Eleanor, find it difficult to hide their disappointment while Blair hatches another underhanded plan to get rid of Roman for good. Meanwhile, Jenny and Vanessa help Serena plan the best Christmas surprise ever for Dan, who may have a surprise of his own in mind for Serena. Chuck phones Blair from Europe and informs her that Nate has joined him in Monaco, worrying Blair that Chuck may disclose the details of their hook-up. Also, Rufus refuses to remain the understanding husband any longer after Alison's former lover calls the house.
Season 1, Episode 12: School Lies
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. Everyone agrees to keep a secret pact and say nothing, but it ultimately creates major tension between Serena and Dan, who isn't sure he's ready to take the fall for someone else and risk his future. Meanwhile, Vanessa is working on a documentary project about private schools and accidentally captures Blair and Chuck discussing their affair. Also, Lily contemplates telling Rufus how she really feels about him.
Season 1, Episode 13: A Thin Line Between Chuck and Nate
The shadowy and unseen 'Gossip Girl' takes pleasure in reporting that Serena was spotted by one of GG's Web contacts buying pregnancy tests at a local pharmacy. Of course, on the Upper East Side, the truth is often even juicier and more scandalous than the gossip when Dan's sister, Jenny, learns that Serena was purchasing the tests for Blair who fears she might be pregnant from her trysts with Nate. But things get worse when Nate finds out that Chuck has been having an affair with Blair and both nearly come to physical blows, and Blair becomes ostracized by the rest of her clique as her reputation of a slut becomes more known. Meanwhile, Rufus, in an attempt to cheer himself up following his breakup with Lily, goes on a date with his art gallery sponsor, Bex, to a local bar.
Season 1, Episode 14: The Blair Bitch Project
Spring Break is over, and so are all of Blair's days of hiding away. Finally, after three weeks, she comes back to school, with an unpleasant welcome by Jenny and the "in" crowd, who throw ice cream in her hair. Serena believes that being mean was got Blair kicked out of the "in" crowd in the first place and dethroned "Queen Bee." When Jenny asks Blair to meet her at Butter along with all of Blair's former friends, Serena finds it the perfect opportunity for Blair to show just how nice she is. But the situation goes from nice to sour when Jenny and her friends purposely don't show up, leaving Blair all alone. Meanwhile, Jenny needs something to wear for her 15th birthday party, and eventually ends up stealing one of her friend's mother's dresses in exchange for a $1,200 dress in an exchange shop. But when Jenny tries to get it back, she learns the red dress is over $8,000. Once again, Jenny steals the red dress, throwing her coat over the dress. She comes home to a 15th birthday party created by none other than Blair, who talked to Jenny's dad, and made the birthday party as lame as possible. While Jenny's dad doesn't realize how lame the party is, Jenny's friends do, and are about to leave when they find Jenny wearing the red dress. They ditch the birthday party and meet Blair at Butter. Thinking quickly, Jenny sneaks out and has Nate accompany her to Butter. Jenny's friends are pleased that Nate, who they are attracted to, is hanging out with them, and "forget" the incident with the dress, leaving Blair friendless once again. Also, Serena adjusts to her new living conditions with Chuck, but when she receives inappropriate gifts, she believes Chuck sent them. But, at the very end of the episode, she learns who really sent them, and it wasn't Chuck.
Season 1, Episode 15: Desperately Seeking Serena
Serena's world becomes chaos when a former friend-turned-enemy, the evil and sociopath Georgina Sparks, returns to town and transfers to her school. Dan sees Serena preoccupied and he assumes that it has something to do with the nasty Chuck, who's looking forward to making her life a living-hell as her soon-to-be step-brother. Nate connects with the last person he expected, Vanessa over his failed relationship with Blair. Serena goes out with Georgina for a night on the town to try to patch things up between them, but things get so bad that Serena thinks someone spiked her drink. Meanwhile, Hazel and Penelope try to recruit newcomer Nelly Yuki to be part of their gossip club, but it is not easy. Blair supervises the whole operation and hatches a plan to sabotage Nelly. 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 where Blair tries to repair the damage. Elsewhere, Jenny develops a crush on 16-year-old dog-walker, Asher Hornsby, who might be her ticket to permanent popularity.
Season 1, Episode 16: All About My Brother
Georgina tells Serena that she can reveal a deep dark secret from Serena's past, but no one is prepared for what Georgina does next. Meanwhile, Blair and Jenny's power struggle continues when each of them start spreading false and scandalous rumors about each other on Gossip Girl's blog. Dan sees Jenny's new beau Asher cheating on her and tells her, but Jenny refuses to believe Dan. Rufus goes to Lily for advice on how to handle Jenny's new rebellious behavior. Serena tries to confront Georgina, but she skips town before Serena has a chance. After this, Serena tells Lily and everyone she and Georgina are not friends after discovering that Georgina has been lying to everyone, claiming that she and Serena are still friends.
Season 1, Episode 17: Woman on the Verge
Serena falls back into her old habits of drinking and drugs. She eventually reveals to Blair true reason why she left Manhattan: to avoid being implicated in an accidental drug overdose of a school friend in which Georgina was also present. Blair, Nate, and Chuck are forced to team up to try to help Serena deal with this situation. Unfortunately, Serena is too ashamed at herself to share the truth with Dan about her mistake, and therefore he naturally assumes the worse about his girlfriend. Lily discovers the blackmail videotape Georgina made showing her and Serena that night with their victim. Being who Lily is, she too jumps to the wrong conclusion about Serena and it takes a little intervention from Blair to save her friend from being emotionally torn apart for good. Blair also discovers from Vanessa that Georgina, under her alias 'Sara', is still hounding them by pretending to be their friends, and Georgina takes advantage of Dan's alienation with Serena to make the moves on him. Meanwhile, Rufus is excited when his band is invited to perform at a Rolling Stones sponsored concert. But Lily is the last person on Earth he expects to see at the performance, especially since her wedding rehearsal dinner is on the same night.
Season 1, Episode 18: Much 'I Do' About Nothing
Blair takes matters into her own hands to help Serena deal with the manipulative and evil Georgina Sparks who threatens to expose Serena's secret. Lily, while keeping Rufus in her mind, prepares for her wedding with Bart Bass that is designed to be the Upper East Side's social event of the year. Serena finally tells Dan the whole truth about her past and about Georgnia and they try to work things out. But Dan is guilt-ridden after having cheated on Serena with Georgina and wonders if it is already too late. An unexpected guest shows up at Lily and Bart's wedding. Also Blair manipulates matters so that Georgina goes "somewhere where she can do no harm". As the end of the school year approaches, Blair plans to go somewhere with Chuck.