Season 1, Episode 1: Pilot19 September 2007
The privileged prep school teens on Manhattan's Upper East Side learn that Serena van der Woodsen is back in town, though her reasons for returning are mysterious.
26 September 2007
In the wake of the scandalous Kiss on the Lips party, Serena receives an icy cold reception from Blair.
Season 1, Episode 3: Poison Ivy3 October 2007
As the teens prepare for Ivy League college representatives to visit their campuses, Blair uncovers a secret about Serena; Dan sets his sights on impressing the Dartmouth representative; Jenny and Eric hit it off; Rufus asks Lily a favor.
9 October 2007
Blair is thrilled when her mother, Eleanor, chooses her to be the new face of her clothing line; Serena and Dan are reminded once again that they come from two very different worlds; Nate and Chuck indulge in a boys' weekend to blow off steam after Ivy Week.
Season 1, Episode 5: Dare Devil16 October 2007
Dan makes elaborate plans to impress Serena on their first official date; Jenny is invited to the infamous Blair Waldorf sleepover and finds herself in a high-stakes game of truth or dare; Lily discovers Eric missing from his treatment center, and seeks help from her ex-boyfriend, Rufus.
24 October 2007
Dan's childhood pal Vanessa returns to town and tells him she wants to be more than friends; Blair does her best to keep party crashers out of the masquerade ball, but a disguised Dan and Jenny sneak in; Lily hopes to provoke jealousy in Bart by asking Rufus to be her date at an event.
7 November 2007
Serena and Dan finally acknowledge they are crazy about each other; Jenny discovers a secret about her parents; Blair is once again devastated by Nate's actions.
14 November 2007
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.
28 November 2007
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 Woodsen 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.
5 December 2007
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.
19 December 2007
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.
2 January 2008
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.
9 January 2008
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.
21 April 2008
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.
28 April 2008
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.
5 May 2008
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.
12 May 2008
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.
19 May 2008
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.
1 September 2008
As the summer of the Upper East Siders comes to a close, Blair returns from her summer trip to Europe with a charming new boyfriend, named James, just to make Chuck jealous when she takes him to the Hamptons to spend the last few weeks of the summer with her. However, 'James' is hiding a secret of his own from everyone. Serena, struggling to get over her breakup with Dan, takes a liking to a young lifeguard. Meanwhile, Nate gets involved in a steamy relationship with an older woman, named Catherine whom is married. While Rufus is still on tour with his band, Dan has remained in New York to take a job with a demanding magazine editor, and has gone on a dating spree to get over his breakup with Serena, while Jenny has taken a job at a fashion company working under the cynical, devil-incarnated Laurel, who holds Jenny back for she sees ambitious interns as a threat to her own job.
7 September 2008
As Blair struggles to adjust herself to her British boyfriend, Lord Marcus Beaton's ways, he introduces her to his parents, where the identity of Lord Marcus' mother is revealed. At the Beaton party, Chuck tries to make Blair jealous when he shows up with Catherine, Nate's secret love interest. Meanwhile, Nate and Serena get closer while he tries to keep far away from Catherine, while Serena begins to have doubts about re-staring her romance with Dan. Chuck and Marcus Beaton begin an unexpected friendship, and Blair makes a revelation.
15 September 2008
Serena and Dan are trapped in an elevator during a citywide blackout which makes them trying to work out their differences. Meanwhile, Marcus and Blair have problems of their own which is passion. Chuck realizes that he has problems in having no passion with women other than Blair. Elsewhere, Nate struggles with his feelings for Vanessa and Catherine.
22 September 2008
When Dan starts getting cozy with Amanda, the new girl at school, Serena turns to Blair and her minions to step in to sabotage her chances. Vanessa also enlists Blair's help when she finds out a scandalous secret about Catherine.
29 September 2008
As Gossip Girl narrates the so-called Fashion Week where the students of the Upper East Side gather for the annual fund raiser, Blair becomes angry with her mother when she gives Serena and her new socialite friend, Poppy Lifton, front row seats to the Eleanor Waldorf Fashion Show. Hurt and betrayed by both Serena and her mother, Blair decides to sabotage the show. Meanwhile, Dan, also humiliated and shunned by Serena (who has fully returned to her former bad-girl self), starts hanging out with Chuck and his life of parties. Dan quickly learns that living the life of the dark side has its risks. Also, Lily learns a secret that her new husband, Bart Bass, has been keeping from her.
13 October 2008
Serena decides to visit Yale and gets even with Blair. Dan learns that none of his recommendation letters made it to Yale.
20 October 2008
Vanessa begins her own slide on a dark path when she tries to blackmail Blair into being a nicer person, with the photos she took of Catherine and Marcus. Blair then seeks revenge by convincing Chuck to try to seduce Vanessa to steal her phone camera. Meanwhile, Lily and Bart throw an extravagant housewarming party and expect their children to make them proud, but the Serena do not want to follow the rules when she correctly suspects Bart to be influencing Lily to do what he wants for business and self-interest. Elsewhere, Dan and Jenny discover a big secret that Nate has been keeping from them.
27 October 2008
Jenny has a new young model friend, named Agnes, who encourages Jenny to explore her wild side, and also to confront Eleanor Waldorf who is planning to steal Jenny's designs in order to pass them off as her own. Meanwhile, Serena and Dan attend Rufus' latest art opening as friends, but then Serena meets an artist, named Aaron Rose, and the evening gets a little uncomfortable for Dan. Elsewhere, Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined. Also, Jenny begins to have a mutual feelings with Nate as he's staying with her, Dan, and Rufus while searching for a place to live.
3 November 2008
Serena invites Aaron to be her guest at a charity gala honoring Lily and Bart, but after discovering a secret that Aaron has been keeping from her, Serena begins to question whether Aaron is the guy she thought he was. Hoping it will help her chances of getting into Yale, Blair naively agrees to babysit the 15-year-old daughter of a prominent Yale donor. But the teenager, Emma, proves to be more than a handful and Blair begins to suspect that the evening may actually wind up hurting her chances of getting into the college of her dreams. So, Blair forces Serena and Chuck to help her find the trouble making teen when she takes off. Meanwhile, Vanessa discovers the relationship between Nate and Jenny, in which Jenny is planning with Agnes a guerrilla fashion show by crashing Lily and Bart's gala with th hope that it will either launch Jenny's career or ruin her chances of ever being accepted by the industry. Dan angrily tells Nate to move out of the apartment, while Rufus tries to deal with the rebellious Jenny.
10 November 2008
Blair is against the idea of her mother, Eleanor, with a new man in her life, named Cyrus Rose, and she in her natural and evil ways, does everything in her power to make it impossible for them to be together by trying to break them up when Cyrus throws Blair a party for her 18th birthday. Meanwhile, Jenny and Agnes move in together against Rufus protest, while they try to look for a buyer in the wake of Jenny's fashion show. But when Jenny goes behind Agnes back to exclude her from their business when Agnes cannot be counted on for her slacking off, Agnes learns about Jenny's betrayal and retaliates by setting fire to all of Jenny's designs and throws her out onto the street. Elsewhere, Serena and Aaron fall for each other, but something about Aaron threatens to ruin their new relationship as well as Aaron's father whom happens to be Cyrus. Also, Dan and Chuck are at war again due to Dan's true interest in Chuck's father Bart over his past business deals.
17 November 2008
As Thanksgiving draws near, Blair looks forward to spending the holiday with her family. But her disappointment only begins when her father, Harold, is delayed in trying to leave Europe, and Eleanor's new boyfriend, Cyrus, takes over planning the traditional Thanksgiving feast. Blair also learns that Cyrus plans to propose marriage to Eleanor, which prompts her to run into the company of her Polish maid, Dorota. Serena continues to hide her sordid past from Aaron after he tells her that he too is a recovering alcoholic and party guy. Meanwhile, Dan asks Lily to help intervene in the continuing feud between Jenny and Rufus when Jenny crashes at Lily's penthouse and confides in her that she has decided to file a petition to become legally emancipated from her father. Eric also learns from Chuck about Bart's investigation and files he keeps on everyone to keep everyone and everything under his iron thumb. Elsewhere, Nate's fugitive father, Howie 'The Captain' Archibald, arrives in town to visit him and his mother with an offer to live a life of luxury as fugitives, while Vanessa gets caught up when the authorities comes to call her on Mr. Archibald's whereabouts after he's spotted re-entering the country.
1 December 2008
The teens prepare for the annual Snowflake Ball, a charity event for prep school seniors.
8 December 2008
The entire Upper East Side of Manhattan is rocked when Bart Bass dies suddenly in a limo accident. Serina and Eric takes 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 her latest marriage to Aaron's father Cyrus.
5 January 2009
Because Chuck has been missing since his father's funeral, his Uncle Jack, Bart's younger brother, arrives in New York to help Lily find and help him. Trying to forget her last unpleasant conversation with Chuck, Blair focuses on being accepted into the most prestigious ladies club in the city, the Colony Club. Meanwhile, Jenny returns to school at Constance Billard and immediately takes on Penelope, Hazel, Nelly, Isabel, and the rest of the mean girls. But Jenny is not willing to go down without a valiant Gossip Girl-worthy fight against these bullies.
12 January 2009
At the reading of Bart Bass' will, Chuck is bequeathed the majority share of Bass Industries, but Jack soon manipulates Chuck into giving him the company. Chuck decides to take over the company after being persuaded by Blair. Blair throws a surprise party for Chuck and invites the board of the Bass company. Jack sabotages the party leading the board to elect Jack as the president. Meanwhile, Rufus and Lily travel to Boston to look for their out-of-wedlock son by trying to make contact with the adoptive parents, but they are eventually deceived into thinking their child is dead. Back in New York, Serena's relationship with Dan is almost ruined when she finds out about the half-sibling she shares with him.
19 January 2009
Serena, Blair, Dan, and the rest of the seniors try to find out who is worthy of an early admission to Yale. Serena discovers that she has been accepted, but concedes the acceptance to let Blair take the position because of what Blair will do as a result. Serena also connects with a young new Shakespeare teacher, Rachel Carr, who has no clue about what is going to happen when she gives Blair the first 'B' grade in her life, but Blair soon comes to learn that she may have met her match against this latest addition to her school. Meanwhile, Chuck reluctantly joins forces with Lily in his war against his manipulative Uncle Jack over controlling Bass Industries. Also, Nate and Vanessa plan to take their romance public by attending a romantic night date at the opera, while Lily wants to do the same with Rufus despite his loathing of the wealthy high-society world, and of her reputation in the community over recent events.
2 February 2009
The twisted Blair plans a cruel revenge against her teacher, Rachel Carr, for her one bad grade, but has problems getting her posse of mean girls to rally for support since they are not keen to taking on a teacher. So, Blair starts a rumor that Miss Carr and Dan are romantically involved, which creates a firestorm of gossip, and she has her father, Harold, to back her up. But the final blows comes when Serena sees Dan and Rachel meeting at a local coffee shop and jumps to the wrong conclusion which Blair sees off her greatest victory, but also her most bittersweet one. Meanwhile, Chuck calls upon Nate and Vanessa for help when he wakes up in a strange hotel room and seek out a mysterious woman he met at a mysterious secret society party the night before which may had drastic consequences for him.
16 March 2009
As Constance Billiard prepares for the annual school play of 'Age of Innocence' the frantic production threatens to break the whole school apart as, Dan continues to ignore Serena and continue his dirty tryst with Rachel Carr. When Blair learns that her acceptance into Yale went to Nelly, she suspects Serena of leaking info about her detention stint, while Serena blames Blair of babbling about her own problems. But the real culprit it Rachel who is seeking to get back at Blair for destroying her career. Rufus and Jenny learn about Dan's relationship with Rachel Carr and try to force him to end it. Nate becomes jealous when he thinks that Vanessa is flirting with the play director Julian, while it is Serena who has the crush and asks Vanessa for pointers Meanwhile, Chuck becomes more intrigued and frustrated as he tries to dig deeper into the mystery about his late father and what connections he had with the super-secret underground society which leads him to try to find the shadowy Elle, who warned him about investigating the secret society.
23 March 2009
Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf existence in favor of a wild, unpredictable lifestyle that includes Carter, causing Serena and Chuck to have serious concerns about their friend. Vanessa convinces Nate that it may be time to forgive and forget when it comes to his mother's Kennedyesque family, The Vanderbilts, who abandoned Nate and his mother when they needed them most. Elsewhere, in a misguided effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers.
30 March 2009
Serena decides to throw Jenny an intimate party for her 16th birthday, but things get out of control when Serena's friend Poppy Lifton, returns and turns the small gathering at the van der Woodsen apartment into a huge social event. Meanwhile, Vanessa agrees to help Chuck with a scheme that will make Blair and Nate jealous... and they end up having sex in the process. Also, Rufus learns that Dan and he will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education, in which Lily offers to help. Elsewhere, Dan receives a letter from Boston from Rufus and Lily's illegitimate son wanting to meet with him.
20 April 2009
Serena returns from her week-long trip to Spain with Poppy and Gabriel. But Serena becomes worried that during the hard partying in the country, she thinks she may have gotten married to Gabriel by accident. Meanwhile, Blair makes a secret deal with Nate's grandfather, William, to influence Nate to attend Yale when he decides to defy his grandfather and attend Columbia University in New York City instead. Later, Nate learns some disturbing information about his father's arrest while he is asked to be the best man at his cousin Trip's upcoming wedding. Chuck continues his debauched lifestyle of one-night stands while Jenny decides to make a stand for herself against the loathsome guy. Elsewhere, Dan takes a job as a waiter to earn money for college. H is distressed to find out that the job is a Passover Seder at the Waldorf penthouse that Cyrus holds, and on top of that... several of his friends and family are guests, including his father Rufus.
27 April 2009
Georgina Sparks returns to the Upper East Side after undergoing a major transformation from a born-again Christian camp. Chuck and Nate find themselves at a major crossroads in their relationship as it pertains to their mutual interest in Blair. Serena finds her relationship with Gabriel growing more complicated, when Blair and Chuck discover that he is still with Poppy. Meanwhile, Dan and Vanessa will get drunk playing "I never...". Also, Chuck and Blair try to recruit the redeemed Georgina for their help to deal with Serena's complication with Gabriel. Elsewhere, Rufus confides in Jenny about his desire to propose marriage to Lily.
3 May 2009
Blair pressures Georgina into making amends for her past bad behavior by helping her in a scheme to rip off Poppy after she has embezzled all of the investment money that she and Gabriel claim to invest in. Meanwhile, the rivalry between Nate and Chuck over Blair comes to a head. When Lily learns that Poppy scam ed her of Rufus's investment money, she hatches a secret plan to help Rufus with Dan's college tuition in order to cover up Poppy's scam out of shame. But Serena has a plan to make Poppy pay for all the cheating he did, but Lily is not in agreement and takes drastic measures which ruins everything.
10 May 2009
Lily recalls her past when in a flashback to 1983, the naive and sheltered 17-year-old Lily Rhodes got kicked out of her Santa Barbara boarding school. She ran away to Los Angeles where she tried to re-connect with her divorced and dysfunctional parents; her workaholic record producer father, Rick Rhodes, and the superficial Cece. Lily also met and hooked up with her outgoing free-spirited 19-year-old sister Carol. Carol was the so-called "black sheep" of the family who introduced Lily to the life of partying, as well as Owen, a busboy at Carol's place of employment. Eventually, they all got arrested after crashing a party hosted by the cynical and mean music producer Keith van der Woodsen (Lily's future husband) whom attempted to swindle Carol out of a music deal. In present day New York, Blair and Nate decide to attend their senior prom together. But the evening doesn't turn out exactly as planned, when the Mean Girls attempt to rig the votes for prom king and queen. But Chuck comes to Serena's rescue. Meanwhile, Serena becomes furious when she learns that Lily deliberately had her arrested for her defiance, while Rufus ponders his life and future without Lily, who he snubs for what she did to Serena, as does Eric, Jenny, and even Dan as well whom is forced to bail Serena out of jail himself.
17 May 2009
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; Nelly, Isabel, Penelope, etc, challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year. Meanwhile, Lily and Rufus finally makes amends meet and get engaged and move in together. With Blair's blessing, Jenny becomes the new queen. Chuck finally admits his love to Blair and the two reconcile. As the summer draws near, Nate decides to go on the backpacking trip with Vanessa. Georgina returns to town having recovered/re-stole all of Dan's money, and she also requests Blair for a roommate at NYU. Carter Baizen also shows up and reveals to Serena where her biological father is. In the end, Serena is going to Brown, Blair, Dan, Vanessa, and Georgina are going to NYU, and Nate is going uptown to Columbia, and Lily and Rufus' illegitimate son, Scott, inconspicuously arrives in town for college and to shadow Dan.
14 September 2009
As the summer is drawing to a close, Blair and Chuck are madly in love and adjusting to their new "in a relationship" status, breaking all the traditional rules of dating as would be expected. Serena returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen. Nate returns from his travels with a mysterious brunette, Bree Buckley in tow. Rufus, Dan and Jenny spent the summer in the Hamptons, adjusting to the van Der Woodsens' glamorous lifestyle surprisingly faster than any of them expected. Meanwhile, Vanessa begins a relationship with Scott, not knowing that is the lost brother of Dan and Serena.
21 September 2009
Blair, who is determined to maintain her Queen status in college, embarks on her first day at NYU, along with Dan and Vanessa. Unfortunately, Georgina turns up as Blair's roommate in the dorms, determined to make Blair a social outcast. As Serena prepares to depart for Brown, she and Chuck have a major falling out, so she recruits Chuck's enemy, Carter, to help her get even. Nate and Bree decide to explore their relationship further, knowing full well that it could cause tension between their families who are political rivals.
28 September 2009
It's an Upper East Side face-off when Blair and Chuck both set their sights on a particular item up for bid at Sotheby's and the personal stakes are high. Serena suspects that Carter may be up to his old habits, Georgina takes an interest in Dan, and Vanessa begins to suspect that something isn't quite right with Scott.
5 October 2009
On the first day of school at Constance Billard, Jenny is forced to make her rightful place as the new Queen Bee of the Mean Girls. Unfortunately for Jenny, Blair is more than happy to intervene when news reaches her that Jenny may need her help. Meanwhile, Lily finally returns home to Rufus and her family to find that things are definitely not as she left them, especially after learning that Serena has decided against going to Brown University. Elsewhere, a famous teenage movie actress, Olivia Burke, enrolls at NYU and is assigned as Vanessa's new roommate in which Olivia hopes for a somewhat normal college experience. Also, Olivia's best friend Ursula, another actress co-starring in Olivia's latest movie, befriends Serena.
12 October 2009
Lily and Rufus decide to move up their wedding to the next day, but a series of complications threaten to tear them back apart again. Meanwhile, Chuck discovers a secret that Carter has been keeping from Serena which involves Nate's girlfriend Bree and her family who are out to get Carter. Dan and Vanessa are pulled into one of Georgina's schemes when she threatens to ruin Lily and Rufus' wedding by revealing the secret about Scott Rosson as their illegitimate son. Also, Blair is suspicious of Bree and shares her concerns with Nate that she may have an agenda regarding him and Carter.
19 October 2009
Vanessa and Blair both take to scheming to be given the honor of giving the freshman toast at NYU. Meanwhile, Serena and Nate try their hand at poker in hopes of winning Carter back from the Buckleys, and Dan wants to introduce Olivia to Rufus and Lily.
26 October 2009
Chuck decides to move up his hotel nightclub's opening and enlists Serena's help to get the word out to her celebrity clients for publicity reasons. Feeling left out of the planning, Blair attempts to win Chuck's approval by secretly helping him with a problem concerning opening night. Meanwhile, Dan is unnerved when he finally watches one of Olivia's infamous simulated sex scenes in one of her movies with co-star and real-life boyfriend at the time, Patrick Robinson. Jenny is forced to choose between her friendship with Eric and her new role as Queen Bee of Constance Billiard since she and the Mean Girls are not required to have any friends, except the ones their own vicious and cynical circle. Elsewhere, Rufus gets Lily into the Halloween spirit by taking her out to a costume party.
2 November 2009
Olivia says something she regrets during her appearance on Jimmy Fallon's TV talk show and tries to keep Dan from finding out. With the local election day around the corner, Nate suspects that his grandfather will stop at nothing to get his cousin 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.
9 November 2009
Jenny sets her sights on landing the hottest escort for Cotillion. Dan is upset when Olivia (HILARY DUFF) contemplates leaving school. All-girl French band PLASTISCINES performs.
16 November 2009
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. Meanwhile, 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.
30 November 2009
As Thanksgiving draws near, Blair suspects her mother, Eleanor, has been keeping a big secret from her, but it turns out to be something else entirely. Meanwhile, Vanessa is supposed to spend Thanksgiving with her parents, but has a fight with her picky and estranged mother and she ends up going to Dan's loft. Rufus discovers that Lily has been lying to him about the true nature of her mother Cece's health. Chuck tells Nate that he has some potentially damaging information about one of their friends: Serena whom is caught in a compromising position with Trip Vanderbilt. Elsewhere, Jenny learns that Eric was behind her very public embarrassment at Cotillion and can't pass up a chance to get even with him in the most cruel way, which makes her appear even more vile and twisted than everyone else around her. Also, Serena is put in a very awkward position when Lily invites Trip and his wife, Maureen, to join them for Thanksgiving dinner at their penthouse, and Maureen may know a lot more about what is going on between Trip and Serena than she claims to, and Doroda is revealed to be hiding a secret of her own involving Vallini.
7 December 2009
On the anniversary of Bart Bass' death, Chuck wrestles with the dilemma of following his conscience, or that of his father. Serena begins to suspect in Trip, when thank Nate, discovers that has been joined by Maureen. Dan and Vanessa attempt to navigate their newly complicated friendship. Eric and Kira make work his plan to dethrone Jenny. Meanwhile, the relationship between Lily and Rufus deteriorates when he discovers the letter from Serena's father.
8 March 2010
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 she realizes that his plan is ruined by a memory of the school. Dan tries to overcome the confession of love for Vanessa, without any result. Rufus returns from a ski trip and tries his best to avoid Lily.
15 March 2010
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.
22 March 2010
Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have sex with her. Lily thinks to tell the secret that she has supported conceal, but after a call, she changes of mind. Dan and Vanessa explore a new stage of their friendship. Chuck is forced to make an extremely difficult decision about his hotel. Meanwhile, Serena and Nate have a fight that is reminiscent of past events.
29 March 2010
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.
5 April 2010
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.
12 April 2010
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.
25 April 2010
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.
2 May 2010
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.
10 May 2010
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.
17 May 2010
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.
13 September 2010
After having spent her Parisian summer alone (and in Serena's shadow), Blair hopes to change things when she meets a handsome young man who may be a real prince. But Serena has news that may only increase Blair's insecurity. Meanwhile, back in New York, Georgina and Dan's secret comes to light, and Nate meets a girl who seems refreshingly down to earth after a summer of Chuck Bass-rejects. And speaking of Chuck, he's still missing in action, which causes Lily to worry.
20 September 2010
Blair is pursued by a handsome young man she suspects is part of Monaco's royal family. Chuck adjusts to a fresh start in Paris with a mysterious new woman, Eva.
27 September 2010
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.
4 October 2010
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.
11 October 2010
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.
Season 4, Episode 6: Easy J25 October 2010
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.
1 November 2010
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.
8 November 2010
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.