Rufus (Matthew Settle) and Lily (Kelly Rutherford) grow suspect of Jenny's (Taylor Momsen) relationship with Damien (guest star Kevin Zeggers). Chuck (Ed Westwick) learns more about the woman (guest star Laura Harring) who may or may not be his mother. Dan (Penn Badgley) and Vanessa (Jessica Szohr) struggle through the awkwardness of dating other people. Andrew McCarthy directed the episode written by Amanda Lasher & Robby Hull.
Nate (Chace Crawford) and Serena (Blake Lively) decide to explore the boundaries of their friendship. Blair (Leighton Meester) suspects that Chuck (Ed Westwick) is having problems forgetting about the woman (guest star Laura Harring) he saw at his father's grave. Jenny (Taylor Momsen) agrees to accompany Damien (guest star Kevin Zegers) to a State Dinner but is unaware that he needs her help with a drug exchange. Vanessa (Jessica Szohr) and Dan (Penn Badgley) attempt to move past the awkwardness of Dan's confession of love. Rufus (Matthew Settle) returns from a ski trip and tries his best to avoid Lily (Kelly Rutherford). Tony Wharmby directed the episode written by Sara Goodman.
On the anniversary of Bart Bass' death, Chuck wrestles with an issue from the past and a serious car accident rocks the Upper East Side. Dan and Vanessa attempt to navigate their newly complicated friendship. When Jenny is accused of beating up one of her classmates, Eric is faced with a tough dilemma. Blake Lively, Leighton Meester, Chace Crawford, Kelly Rutherford and Matthew Settle also star. Jason Ensler directed the episode written by executive producer Stephanie Savage.
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 dorm room. 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. 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.
Hoping to impress the elitist theater kids at NYU, Blair (Leighton Meester) sets her sights on landing a private concert with the hottest musical performer of the year, Lady Gaga. Dan (Penn Badgley) and Olivia (guest star Hilary Duff) sign up to write and star in a school play, based on an idea by Blair and directed by Vanessa (Jessica Szohr). With Blair out of the picture, Serena (Blake Lively) turns to Nate (Chace Crawford) to help her get through a difficult situation. As a favor to Chuck (Ed Westwick), Jenny (Taylor Momsen) agrees to hang out with Damien (guest star Kevin Zegers), 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. Kelly Rutherford and Matthew Settle also star. Tony Wharmby directed the episode written by Leila Gerstein.
Not satisfied with just being Queen of Constance Billard, Jenny (Taylor Momsen) sets her sights on becoming the Queen of all the Upper East Side by landing the hottest escort for Cotillion. Nate (Chace Crawford) and Chuck (Ed Westwick) plot to help Serena (Blake Lively) and Blair (Leighton Meester) repair their damaged friendship. Dan (Penn Badgley) is upset when Olivia (guest star Hilary Duff) contemplates leaving school for a movie project. Jessica Szohr, Kelly Rutherford and Matthew Settle also star. Alison McLean directed the episode written by Amanda Lasher.
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.
In need of publicity for his new hotel, Chuck decides to move up his club’s opening and enlists Serena’s help to get the word out to her celebrity clients. Feeling left out of the planning, Blair attempts to win Chuck’s approval by secretly helping him with a problem concerning opening night. Dan is unnerved when he finally watches one of Olivia’s infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson. Jenny is forced to choose between her relationship with Eric and her new role as Queen Bee. Rufus gets Lily into the Halloween spirit.
Vanessa (Jessica Szohr), hoping to finally win her mother Gabriela's (guest star Gina Torres) approval, desperately vies with Blair (Leighton Meester) for the honor of delivering the freshman toast at NYU, but at what price? Dan (Penn Badgley) invites Olivia (guest star Hilary Duff) to meet Rufus (Matthew Settle) and Lily (Kelly Rutherford), which leads to all sorts of problems for the new couple. Serena (Blake Lively) and Nate (Chace Crawford) team up to help Carter Baizen (guest star Sebastian Stan). Taylor Momsen and Ed Westwick also star. John Stephens directed the episode written by Jake Coburn.
Lily (Kelly Rutherford) and Rufus (Matthew Settle) decide to move up their wedding to the next day, but will someone or something come between them before they become man and wife? Chuck (Ed Westwick) discovers a secret that Carter (guest star Sebastian Stan) has been keeping from Serena (Blake Lively). Dan (Penn Badgley) and Vanessa (Jessica Szohr) are pulled into one of Georgina's (Michelle Trachtenberg) schemes. Blair (Leighton Meester) is suspect of Bree (guest star JoAnna Garcia) and shares her concerns with Nate (Chace Crawford). Taylor Momsen also stars. Ron Fortunato directed the episode written by Leila Gerstein. Fortunato directed the episode written by Leila Gerstein.
It's the first day of school at Constance Billard which means it's also time for Jenny to take her rightful place as the new Queen Bee. Unfortunately for Jenny, Blair is more than happy to intervene when news reaches her that she may be needed back at Constance. Meanwhile, Lily returns home to Rufus and her family to find that things are definitely not as she left them. Plus, a famous movie actress, Olivia Burke (recurring guest star HILARY DUFF - A Cinderella Story, Material Girls, Lizzie McGuire), enrolls at NYU in hopes of having a somewhat normal college experience, and is assigned to be Vanessa's roommate. Guest star TYRA BANKS (The Tyra Show, America's Next Top Model) appears as Ursula, an actress co-starring in Olivia's movie and someone who Serena befriends.
It's an Upper East Side face-off when Blair (Leighton Meester) and Chuck (Ed Westwick) both set their sights on a particular item up for bid at Sotheby's and the personal stakes are high. Serena (Blake Lively) suspects that Carter (guest star Sebastian Stan) may be up to his old habits, Georgina (Michelle Trachtenberg) takes an interest in Dan (Penn Badgley), and Vanessa (Jessica Szohr) begins to suspect that something isn't quite right with Scott (guest star Chris Riggi). Chace Crawford, Taylor Momsen and Matthew Settle also star. Jean DeSegonzac directed the episode written by Robert Hull.
Blair (Leighton Meester), who is determined to maintain her Queen status in college, embarks on her first day at NYU, along with Dan (Penn Badgley) and Vanessa (Jessica Szohr). Unfortunately, Georgina (guest star Michelle Trachtenberg) turns up as Blair's roommate in the dorms, determined to make Blair a social outcast. As Serena (Blake Lively) prepares to depart for Brown, she and Chuck (Ed Westwick) have a major falling out, so she recruits Chuck's enemy, Carter (guest star Sebastian Stan), to help her get even. Nate (Chace Crawford) and Bree (guest star JoAnna Garcia) decide to explore their relationship further, knowing full well it could cause tension between their families who are political rivals. Taylor Momsen and Matthew Settle also star. Norman Buckley directed the episode written by Amanda Lasher.
As the summer is drawing to a close, Blair (Leighton Meester) and Chuck (Ed Westwick) are madly in love and adjusting to their new "in a relationship" status, breaking all traditional rules of dating as would be expected. Serena (Blake Lively) returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen (guest star Sebastian Stan). Nate (Chace Crawford) returns from his travels with a mysterious brunette, Bree Buckley (guest star JoAnna Garcia) in tow. Rufus (Matthew Settle), Dan (Penn Badgley) and Jenny (Taylor Momsen) spent the summer in the Hamptons, adjusting to the van der Woodsen's glamorous lifestyle surprisingly faster than any of them expected. Jessica Szohr also stars. J. Miller Tobin directed the episode written by Joshua Safran.
Gossip Girl decides to send a shocking email blast in the graduation ceremony of Constance Billard and St. Jude's, pushing Serena to device a devious plan of attack. The Mean Girls Club challenge Jenny to succeed Blair as Queen Bee for next year. Lily and Rufus struggle with their relationship after Lily's betrayal. As for the cliffhangers, Blair and Chuck finally...and Serena is shocked by...and Georgina decides to...and Dan, Nate and Vanessa unknowingly...
In a flashback to the 80s, 17-year-old Lily Rhodes (Brittany Snow) gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her parents, Rick (Andrew McCarthy) and Cece (Cynthia Watros), and sister, Carol (Krysten Ritter). Back in present day, Blair and Nate attend prom together, but the evening doesn't turn out exactly as planned and Chuck and Serena have a little something to do with that. Serena and Lily don't see eye-to-eye over Serena's recent run-in with the law. No Doubt performs in the flashbacks as an 80s band called "Snowed Out."
Blair puts pressure on Georgina to making amends for her past bad behavior by helping her in an evil plan. The rivalry between Nate and Chuck over Blair reaches a boiling point. Lily makes a secret plan to help Rufus with Dan's college tuition.
Georgina returns to the Upper East Side but it's not the same Georgina we all knew, she's changed. Chuck and Nate relationship is at a crossroad because of their mutual interest in Blair. Serena relationship with Gabriel get's more complicated.
Serena returns from her trip to Spain with Poppy and Gabriel. Blair makes a secret deal with Nate's grandfather. Dan takes a job to earn money for college.
Serena throw's Jenny an small birthday party for her sweet sixteenth, but things get out of control when Poppy Lifton turns the birthday into a huge social event. Vanessa in a moment of desesperation agrees to help Chuck with a scheme having to do with Blair and Nate. Rufus tries to figure out how to cover Dan's Yale tuition, when he learns that Dan will not receive financial aid.
Devastated by the recent plot twist in her life, Blair (Leighton Meester) turns her back on her predictable Waldorf existence in favor of a more wild and unpredictable lifestyle, causing Serena (Blake Lively) and Chuck (Ed Westwick) to have serious concerns about their friend. Vanessa (Jessica Szohr) convinces Nate (Chace Crawford) 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. In a misguided effort to be completely honest with each other, Lily (Kelly Rutherford) and Rufus (Matthew Settle) agree to share lists of their past lovers. Penn Badgley and Taylor Momsen also star. J. Miller Tobin directed the episode written by Robby Hull & Etan Frankel.
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.
The students find out who is worthy of an early admission to Yale. Serena connects with a new Shakespeare teacher, who has no clue about what is going to happen when she gives Blair the first B grade in her life. Chuck pairs up with an unlikely ally in his battle over Bass Industries. Nate and Vanessa have a romantic night at the opera.
In the reading of Bart's will, Chuck, Bart's brother, Jack and Lily learn that Chuck is now the CEO of Bass Industries. Chuck agrees that Jack became his guardian. Rufus and Lily's relationship is strained as Rufus searches for details about the child he never knew he had. Noticing the strange way his father has been acting lately, Dan does some investigating and uncovers Rufus and Lily's secret, and he has to decide now what to do and who to tell the shocking revelation.
This episode will see Chuck having a hard time dealing with his father's death, and runs away to Bangkok before his uncle Jack Bass brings him back to New York and to a worried Blair. While Jack tells Lily he wants to be Chuck's legal guardian, Chuck gets in trouble in school for smoking hash. Though headmistress Queller agrees to forget the whole incident if Chuck doesn't smoke again, Chuck lights up a joint in the office.
A sudden and tragic event impacts the lives of our favorite Upper East Side teens and their parents. Blake Lively, Leighton Meester, Penn Badgley, Chace Crawford, Taylor Momsen, Ed Westwick, Kelly Rutherford and Matthew Settle star. Joe Lazarov directed the episode written by Stephanie Savage.
Chuck and Blair make a bet to choose the perfect date for each other for the annual Snowflake Ball. Lexi has her sights set on Dan leaving Serena confused with her feelings. Nate and Vanessa are forced to be together leaving their emotions and friendship in danger of being burnt.
It's Thanksgiving time and Blair is offended when her Mom's new man hijacks her Thanksgiving traditions. Lily attempts to fix Jenny and Rufus's frail bond. Eric discovers a secret on Bart.
Blair (Leighton Meester) does not approve of the new man, Cyrus Rose (guest star Wallace Shawn), in her mother's (guest star Margaret Colin) life, so she makes it her mission to break up the lovebirds by any means necessary. Jenny (Taylor Momsen) moves in with Agnes (guest star Willa Holland) as the friends move forward with their plans for a fashion line. Serena (Blake Lively) continues to fall for the new guy in her life, Aaron (guest star John Patrick Amedori), but she learns something about him that threatens to end things just as they are getting really good. Dan (Penn Badgley) decides to win the trust of Bart Bass (guest star Robert John Burke) in order to learn more about the man and possibly write an expose on him for Vanity Fair, but things get heated after Chuck (Ed Westwick) finds out the real reason Dan is spending so much time around his family. Matthew Settle also stars. David Von Ancken directed the episode written by Jessica Queller.
Serena (Blake Lively) invites Aaron (guest star John Patrick Amedori) to be her guest at a charity gala honoring Lily and Bart (Kelly Rutherford and guest star Robert John Burke), but after discovering a secret that Aaron has been keeping from her she begins to question whether Aaron is the guy she thought he was. Hoping it will help her chances of getting into Yale, Blair (Leighton Meester) naively agrees to babysit the 15-year-old daughter of a prominent Yale donor, but the teenager 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. Meanwhile, Jenny (Taylor Momsen) and Agnes (guest star Willa Holland) plan a guerilla fashion show that will either launch Jenny's star or ruin her chances of ever being accepted by the industry. Penn Badgley, Chace Crawford, Ed Westwick, Jessica Szohr and Matthew Settle also star. Michael Fields directed the episode written by Etan Frankel & John Stephens.
Jenny has a new young model friend, Agnes, who encourages Jenny to explore her wild side, and also to confront, Eleanor Waldorf, who is attempting to "borrow" Jenny's designs. Meanwhile Serena and Dan attend Rufus art opening as friends, but then Serena meets an artist, Aaron Rose, and the evening gets a little uncomfortable. Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined.
Vanessa tries to blackmail Blair into being a nicer person, with the pictures of Catherine and Marcus. Blair then seeks revenge by convincing Chuck to try to seduce Vanessa. Lily and Bart throw an extravagant housewarming party and expect their children to make them proud, but Serena do not want to follow the rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.
After Blair (Leighton Meester) and Serena (Blake Lively) get into a catfight, Serena decides to get even with Blair, who has always dreamed of attending Yale, by ditching her plans to visit Brown, and instead accepting the Dean of Yale's personal invitation to visit the school. After discovering that none of his recommendation letters for Yale were ever submitted, Dan (Penn Badgley) frantically tries to figure out a way to salvage his chances of getting into the school. While on the Yale campus, Chuck (Ed Westwick) is kidnapped by a group of Skull and Bones members and Nate (Chace Crawford) hooks up with a co-ed. Taylor Momsen, Jessica Szohr, Kelly Rutherford and Matthew Settle also star. Norman Buckley directed the episode written by Alexandra McNally & Joshua Safran.
Fashion Week is here!!! Blair is furious with her mother for giving Serena and her new socialite friend, Poppy Lifton, front row seats to the Eleanor Waldorf show. Hurt by both Serena and his mother Blair decides to sabotage the show. Meanwhile, Dan starts hanging out with Chuck, but he quickly learns that the dark side has its risks. Lily learns a secret that her new husband, Bart has been keeping from her.
Blair and her 'Posse' interview different girls to decide whether or not they would be inducted into their 'clique'. Dan bumps into new student Amanda and they form an instant bond however, Blair and her 'posse' attempt to sabotage Dan and Amanda's friendship by inducting her as the new girl in their 'clique' meanwhile, Serena meets a new lust interest and Vanessa meets with the Duchess.
Serena and Dan are trapped in an elevator during a citywide blackout making them work out their differences. Marcus and Blair have problems of their own which is passion. While Chuck has problems in having no passion with women other than Blair. Nate struggles with his feelings for Vanessa and Catherine.
The identity of Lord Marcus' mother is revealed - which leaves our favorite Upper East Siders shocked. Nate and Serena get closer. Chuck and Lord Marcus begin an unexpected friendship and Blair makes a revelation.
In the second season premiere, our favourite Upper East Siders endure the Summer heat in the Hamptons. During the trip in the Hamptons, Blair meets a charming new boy hoping to make Chuck jealous, Nate gets involved in a steamy relationship and Serena questions her past relationship with Dan.
Privileged students at an exclusive Manhattan prep school keep up on local gossip from a secretive blogger. In the pilot epsiode, campus It Girl Serena (Blake Lively) returns just as abruptly and mysteriously as she left one year ago, and her best friend Blair (Leighton Meester) is less than thrilled about this.
Blair tells Serena she knows about her past betrayal, then turns a cold shoulder to her; Chuck hosts a fund-raiser brunch, and Serena decides to take Dan to arch-enemy Chuck's fund-raiser brunch at The Palace, and Jenny seeks advice from Blair, who realizes she may have something to gain by allowing Jenny into her inner circle.
Ivy week equals drama as the Upper East Side teens from Constance Billard and St. Jude's prepare for a much-anticipated visit from the Ivy League representatives, Blair uncovers a scandalous secret about Serena that may not remain a secret much longer.
Meanwhile 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, and Rufus must swallow his pride and ask Lily for a favor to help his son.
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 feelings of betrayal and jealousy when Serena moves into the spotlight and Blair is 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 to blow off steam after Ivy Week.
Dan takes Serena on their first official date and he makes elaborate plans to try an impress her. Meanwhile Jenny is invited to Blair Waldorfs for a sleepover. While there Jenny finds herself in a high-stakes game of "Truth or Dare". Lily goes to see Eric and discovers that he is missing from the treatment center. Lily must enlist the help from her ex-boy toy Rufus.
In this episode we will meet a new love interest for Dan, a 17-year-old artist/filmmaker named Vanessa who hates private school. Vanessa is played by Jessica Szohr. Dan's childhood pal Vanessa returns to town and tells him she wants to be more than friends. Meanwhile, Blair does her best to keep party crashers out of the masquerade ball, but a disguised Dan and Jenny sneak in; and Lily hopes to provoke jealousy in Bart Bass by asking Rufus to be her date at an event.
Serena and Dan finally acknowledge they are crazy about each other, despite their polar opposite worlds that constantly threaten to pull them apart. Chuck contemplates investing in a burlesque club in the hopes of making his hard-to-please father, Bart , proud of him. Nate confronts his father, Captain , about the drugs he found in the house, but his father denies having a problem. Jenny discovers a secret her father, Rufus , and mother, Alison, have been keeping from her. Finally, Blair is once again devastated by Nate?s actions after Jenny reveals that Nate kissed her by accident thinking she was Serena. Nate lands himself in Jail and Bail is 1 Million Dollars, must be pretty serious.
At her 17th-birthday party, Blair attempts to mask her strained relationship with Nate; and Dan invites Vanessa to the party so that she and Serena can bond. Meanwhile, Jenny brings her mom home for a visit, much to Rufus' surprise; and Nate's parents pressure him to make a sacrifice for the good of their family.
This is the episode we meet John Shay, Blair's gay Daddy Harold Waldorf who ran off with the male model. Also in this episode the Humphreys and Van der Woodsens' share Thanksgiving dinner.
Celia Rhodes (Serena's grandmother and Lily's mother) makes an appearance just in time for one of our favorite traditions: Debutante Ball. Celia is said to be in her 60s, very wealthy, manipulative and a larger than life woman who is very set in her ways. A fist fight will occur at the ball. The episode will also feature a Belgian Prince and a New York Times journalist.
Also in this episode we will see our first singing group, The Pierces, a sister act from New York City. They will be playing two of their hit songs "Secret" and "Three Wishes".
Blair's father tells her that he and his boyfriend Roman bought a vineyard in France. Blair feels sad because the day she envisioned spending with her father doesn't turn how she thought it would.
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. Vanessa is working on a documentary project about private schools and accidentally captures Blair and Chuck discussing their affair. Lily contemplates telling Rufus how she really feels about him.
Gossip Girl takes pleasure in reporting that Serena van der Woodsen was spotted 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 that Chuck has been having an affair with Blair.
Having been recently dethroned as Queen Bee, Blair returns to school with the support of her BFF, Serena. Dan visits his mother and upon his return home hes surprised to meet Rufus new girlfriend. She apparently spent the night and is now making pancakes in the kitchen. We see Blair at a club alone at a huge table waiting for her friends to arrive, but no one has shown up yet. Jennys drive to popularity hits when she does something illegal to fit in. The we see her going to sell some of her things to a consignment shop. Serena struggles to adjust to living with Chuck, and receives disturbing packages from an unknown sender.
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.
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 has a chance. After this Serena says that she and Georgina are not friends.
After Georgina reveals the true reason Serena left Manhattan, Serena goes back into her old habits. Her friends Blair, Nate and Chuck in order to help her, have to put their differences aside. Unfortunately, Serena is too ashamed to share the truth with Dan, therefore he assumes the worse about his girlfriend. Meanwhile, Rufus is excited when his band is invited to perform at a Rolling Stone-sponsored concert, but Lily is the last person on earth he expects to see at the performance, especially since her wedding rehearsal dinner is the same night.
Blair takes matters into her own hands to help Serena with the manipulative and evil Georgina Sparks. 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 they try to work things out after Dan has cheated on her, will it be too late? An unexpected guest shows up at Lily and Bart's wedding. Georgina goes somewhere where she can do no harm. Blair plans to go somewhere with Chuck.
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Privileged students at an exclusive Manhattan prep school keep up on local gossip from a secretive blogger. In the pilot epsiode, campus It Girl Serena (Blake Lively) returns just as abruptly and mysteriously as she left one year ago, and her best friend Blair (Leighton Meester) is less than thrilled about this.
Blair tells Serena she knows about her past betrayal, then turns a cold shoulder to her; Chuck hosts a fund-raiser brunch, and Serena decides to take Dan to arch-enemy Chuck's fund-raiser brunch at The Palace, and Jenny seeks advice from Blair, who realizes she may have something to gain by allowing Jenny into her inner circle.
Ivy week equals drama as the Upper East Side teens from Constance Billard and St. Jude's prepare for a much-anticipated visit from the Ivy League representatives, Blair uncovers a scandalous secret about Serena that may not remain a secret much longer. 
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 feelings of betrayal and jealousy when Serena moves into the spotlight and Blair is 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 to blow off steam after Ivy Week.
Dan takes Serena on their first official date and he makes elaborate plans to try an impress her. Meanwhile Jenny is invited to Blair Waldorfs for a sleepover. While there Jenny finds herself in a high-stakes game of "Truth or Dare". Lily goes to see Eric and discovers that he is missing from the treatment center. Lily must enlist the help from her ex-boy toy Rufus.
In this episode we will meet a new love interest for Dan, a 17-year-old artist/filmmaker named Vanessa who hates private school. Vanessa is played by Jessica Szohr. Dan's childhood pal Vanessa returns to town and tells him she wants to be more than friends. Meanwhile, Blair does her best to keep party crashers out of the masquerade ball, but a disguised Dan and Jenny sneak in; and Lily hopes to provoke jealousy in Bart Bass by asking Rufus to be her date at an event.
Serena and Dan finally acknowledge they are crazy about each other, despite their polar opposite worlds that constantly threaten to pull them apart. Chuck contemplates investing in a burlesque club in the hopes of making his hard-to-please father, Bart , proud of him. Nate confronts his father, Captain , about the drugs he found in the house, but his father denies having a problem. Jenny discovers a secret her father, Rufus , and mother, Alison, have been keeping from her. Finally, Blair is once again devastated by Nate?s actions after Jenny reveals that Nate kissed her by accident thinking she was Serena. Nate lands himself in Jail and Bail is 1 Million Dollars, must be pretty serious.
At her 17th-birthday party, Blair attempts to mask her strained relationship with Nate; and Dan invites Vanessa to the party so that she and Serena can bond. Meanwhile, Jenny brings her mom home for a visit, much to Rufus' surprise; and Nate's parents pressure him to make a sacrifice for the good of their family.
This is the episode we meet John Shay, Blair's gay Daddy Harold Waldorf who ran off with the male model. Also in this episode the Humphreys and Van der Woodsens' share Thanksgiving dinner.
Celia Rhodes (Serena's grandmother and Lily's mother) makes an appearance just in time for one of our favorite traditions: Debutante Ball. Celia is said to be in her 60s, very wealthy, manipulative and a larger than life woman who is very set in her ways. A fist fight will occur at the ball. The episode will also feature a Belgian Prince and a New York Times journalist.
Blair's father tells her that he and his boyfriend Roman bought a vineyard in France. Blair feels sad because the day she envisioned spending with her father doesn't turn how she thought it would.
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. Vanessa is working on a documentary project about private schools and accidentally captures Blair and Chuck discussing their affair. Lily contemplates telling Rufus how she really feels about him.
Gossip Girl takes pleasure in reporting that Serena van der Woodsen was spotted 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 that Chuck has been having an affair with Blair.
Having been recently dethroned as Queen Bee, Blair returns to school with the support of her BFF, Serena. Dan visits his mother and upon his return home hes surprised to meet Rufus new girlfriend. She apparently spent the night and is now making pancakes in the kitchen. We see Blair at a club alone at a huge table waiting for her friends to arrive, but no one has shown up yet. Jennys drive to popularity hits when she does something illegal to fit in. The we see her going to sell some of her things to a consignment shop. Serena struggles to adjust to living with Chuck, and receives disturbing packages from an unknown sender.
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.
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 has a chance. After this Serena says that she and Georgina are not friends.
After Georgina reveals the true reason Serena left Manhattan, Serena goes back into her old habits. Her friends Blair, Nate and Chuck in order to help her, have to put their differences aside. Unfortunately, Serena is too ashamed to share the truth with Dan, therefore he assumes the worse about his girlfriend. Meanwhile, Rufus is excited when his band is invited to perform at a Rolling Stone-sponsored concert, but Lily is the last person on earth he expects to see at the performance, especially since her wedding rehearsal dinner is the same night.
Blair takes matters into her own hands to help Serena with the manipulative and evil Georgina Sparks. 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 they try to work things out after Dan has cheated on her, will it be too late? An unexpected guest shows up at Lily and Bart's wedding. Georgina goes somewhere where she can do no harm. Blair plans to go somewhere with Chuck.
