Season 2, Episode 1: Summer Kind of Wonderful
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.
Season 2, Episode 2: Never Been Marcused
Original Air Date—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.
Season 2, Episode 3: The Dark Night
Original Air Date—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.
Season 2, Episode 4: The Ex-Files
Original Air Date—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.
Season 2, Episode 5: The Serena Also Rises
Original Air Date—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.
Season 2, Episode 6: New Haven Can Wait
Original Air Date—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.
Season 2, Episode 7: Chuck in Real Life
Original Air Date—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.
Season 2, Episode 8: Pret-a-Poor-J
Original Air Date—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.
Season 2, Episode 9: There Might be Blood
Original Air Date—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.
Season 2, Episode 10: Bonfire of the Vanity
Original Air Date—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.
Season 2, Episode 11: The Magnificent Archibalds
Original Air Date—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.
Season 2, Episode 12: It's a Wonderful Lie
Original Air Date—1 December 2008
The teens prepare for the annual Snowflake Ball, a charity event for prep school seniors.
Season 2, Episode 13: O Brother, Where Bart Thou?
Original Air Date—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.
Season 2, Episode 14: In the Realm of the Basses
Original Air Date—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.
Season 2, Episode 15: Gone with the Will
Original Air Date—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.
Season 2, Episode 16: You've Got Yale
Original Air Date—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.
Season 2, Episode 17: Carnal Knowledge
Original Air Date—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.
Season 2, Episode 18: The Age of Dissonance
Original Air Date—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.
Season 2, Episode 19: The Grandfather
Original Air Date—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.
Season 2, Episode 20: Remains of the J
Original Air Date—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.
Season 2, Episode 21: Seder Anything
Original Air Date—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.
Season 2, Episode 22: Southern Gentlemen Prefer Blondes
Original Air Date—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.
Season 2, Episode 23: The Wrath of Con
Original Air Date—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.
Season 2, Episode 24: Valley Girls
Original Air Date—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. Season 2, Episode 25: The Goodbye Gossip Girl
Original Air Date—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.
Season 3, Episode 4: Dan de Fleurette
Season 3, Episode 7: How to Succeed in Bassness
