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On the anniversary of Bart Bass death, Chuck has to deal with some issues from the past and a car accident disturbs the Upper East Side. Meanwhile, Dan and Vanessa tried to stay in their complicated friendship no matter what. Jenny is accused of beating a classmate, and Eric has to decide which story to believe.

Blair's bid to find out what her Mother is hiding backfires. Vanessa gets into a fight with her mom and ends up at the Humphreys. Rufus is hurt when he discovers Lily has been lying to him. Chuck divulges some news that could ruin a friend to Nate. Jenny tries to get even with Eric after learning the truth.

Trying to impress NYU theater kids, Blair uses her contacts to get a private concert with today's hottest performer, Lady Gaga. Dan and Olivia sign up to write and star in an NYU play, based on an idea by Blair and directed by Vanessa. Meanwhile, Serena turns to Nate for help in a dificult situation, now that Blair is not there. As a favor to Chuck, Jenny agrees to hang out with Damien, an ambassador's son staying in Chuck's hotel, and the experience turned out to be more intriguing than what she thought.

Jenny wants to be the Queen Bee of not only Constance but of all the Upper East Side, as she lands the hottest escort for the Cotillion. Leighton Meester's new single "Somebody to Love", is featured in the episode, along with performace from Plastiscines.

Olivia as a guest on the Jimmy Fallon's talk show says something she regrets and tries to hide it from Dan. With elections coming up, Nate suspects his grandfather will do everything he has to get Trip on the congress. After another fight with Serena, Blair gets a new friend and takes her to an election night party at Chuck's hotel, just to make Serena jealous.

Looking for publicity for his new hotel, Chuck moves his club's opening and convinces Serena to assist him in getting the word out. Feeling left out, Blair tries to win Chuck's approval by secretly helping him with a problem concerning the opening night. Meanwhile, Dan get's nervous after watching one of Olivia's infamous sex scenes with her co-star and real-life boyfriend during that time, Patrick Robinson. Jenny is forced to choose between Eric and her new role as Queen Bee, which as a result causes major conflict between the two characters.

Vannessa desperately trying to have her mom's approval, teams up with Blair to do the honor of delivering the freshman taost at NYU, but what will be the price she has to pay? Dan takes Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple. Meanwhile, Serena and Nate team up to help Carter Baizen.

Lily and Rufus move up their wedding day, but someone or something will come between them. Can they overcome this and finally get married? Chuck uncovers Carter's secret. Georgina traps Dan and Vanessa into one of her schemes. Blair suspect something not good about Bree and shares her concerns with Nate.

It's Jenny's first day of school at Constance Billard which means it's her time to take her place as the new Queen Bee. But Blair wants to take her spotlight when she is needed back at Constance. Lily returns home to find that everything is different now. Meanwhile, a famous movie actress, Olivia Burke, enrolls in NYU and as Vanessa's new roomate who wants to have a normal college life. Tyra Banks guest stars as Ursula, a co-star in Olivia's movie and Serena's new friend.

Blair and Chuck face-off when the both set their sights on an item up for bid at Sotheby's. Serena begins to think that Carter may have returned to his old habits, Georgina becomes interested in Dan, and Vanessa thinks that something is wrong with Scott.

Blair ends up with Georgina as as her roommate in the dorms at NYU. While Serena and Chuck come to blows, so she joins forces with Chuck's enemy, Carter. Nate and Bree try to take their relationship up a gear despite the animosity between their families.

As the summer ends, Blair and Chuck are madly in love and adjusting to their new "in a relationship" status, breaking all 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. Rufus, Dan and Jenny spent the summer in the Hamptons, adjusting to the Van Der Woodsen's glamorous lifestyle much faster than any of them expected.

When Gossip Girl sends out an e-mail during graduation, Serena must come up with a plan of attack. Meanwhile, The Mean Girls challenge Jenny to be Blair's successor as Queen Bee, and Lily and Rufus work to repair their relationship.

In a flashback to the 1980s, then 17-year-old Lily Rhodes heads to Los Angeles to reconnect with her parents after getting kicked out of boarding school. Meanwhile in present day, Blair and Nate go to their senior prom together, but Chuck ensures the night does not go as planned.

Blair pressures Georgina into making amends for her past bad behavior by helping her in a scheme. The rivalry between Nate and Chuck over Blair comes to a head. Lily hatches 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 might be in for the hugest mistake in her life. During a crazy night out, she said "si" to her new beau...

Serena decides to throw Jenny Humphrey an intimate party for her 16th birthday, but things get out of control when Poppy Lifton turns the small gathering into a huge social event. In a moment of weakness, Vanessa agrees to help Chuck with a scheme to make Blair jealous, while Vanessa sees an opportunity to make Nate jealous at the same time. Rufus learns that Dan will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education. Blair reveals some unresolved feelings between her and Nate.

Devastated by the turn her life has taken, Blair opts for a wild lifestyle instead of her perfect Waldorf life causing Chuck and Serena to become concerned. Vanessa tries to convince Nate that he needs to move on after his mother's family, The Vanderbilts, abandoned him and his mother. Trying to be honest with each other, Lily and Rufus both put together their lists of past relationships.

Nate has a conflict with Vanessa and turns to Blair for help. Chuck is dealing with his father's trouble past. Dan seems to have no grief from his break-up coming from his actions and Lily and Rufus are questioning where their relationship is headed.

Blair comes up with a devious plan to take down her new teacher, Rachel. Chuck has no recollection of what happened to him when he wakes up in a hotel. Nate and Vanessa try to help Chuck fill in the missing pieces of his night.

The students are stressed out as they find out who was accepted and who didn't make the cut for early admission to Yale. Meanwhile, Serena bonds with Rachel, her Shakespeare teacher, who is unaware of what Blair has in store for her following receiving her first B; Chuck finds an unlikely ally in his feud with Jack; and Nate and Vanessa have a romantic evening together.

With the reading of Barts will, Chuck (Ed Westwick), Barts brother, Jack (guest star Desmond Harrington), and Lily (Kelly Rutherford) learn the fate of the Bass empire. Rufus (Matthew Settle) and Lilys relationship is strained as Rufus seeks details about the child he never knew he had. Noticing that his father has been acting strangely as of late, Dan (Penn Badgley) does some investigating and uncovers Rufus and Lilys secret, putting him in the awkward situation of deciding what to do with this shocking revelation and who to share it with. Blake Lively, Leighton Meester, Chace Crawford, Taylor Momsen and Jessica Szohr also star. Tricia Brock directed the episode written by Amanda Lasher

UNCLE JACK BASS ARRIVES ON THE SCENE - With Chuck MIA since his father's funeral, Uncle Jack arrives on the Upper East Side to help Chuck pick up the messy pieces, but first he has to find him. Trying her best to forget her last painful exchange with Chuck, Blair focuses her attention on being accepted into the most prestigious ladies club in the city, Colony Club. Jenny returns to Constance Billard and immediately takes on Penelope and her posse of mean girls, but no one is going down without a valiant Gossip Girl-worthy fight.

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.

Blaire 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.

Blaire is against the idea of her mother with Cyrus Rose a new man in her life and does everything in her power to make it impossible for them to be together. Jenny and Agnes move in together. Serena and Aaron fall for each other but something about Aaron threatens to ruin their new relationship. Dan and Chuck are at war due to Dan's true interest in his father Bart Bass.

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 she 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 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 college of her dreams. Meanwhile, Jenny and Agnes plan a guerilla fashion show that will either launch Jenny's star or ruin her chances of ever being accepted by the industry.

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.

When Blair and Serena get into a fight, Serena decides to get back at Blair by visiting Yale, Blair's dream school, instead of Brown. Meanwhile, Dan learns that his letters of recommendation were never sent to Yale and scrambles to find a way to make sure is chances of getting into the Ivy League school have not been damaged. At Yale, Chuck is taken captive my members of the Skull and Bones society and Nate hooks up with a Yale co-ed.

During Fashion Week, Blair learns that Eleanor, after a suggestion from Jenny, has given Serena and Poppy front row seat to the Waldorf show. Hurt, Blair decides to sabotage the show. Meanwhile, Dan begins hanging out with Chuck, but Dan learns the hard way that Chuck isn't the best company to keep. Elsewhere, Lily finds out the dark secret that Bart has been keeping.

When Serena sees Dan with Amanda, the new girl in school, Blair takes it upon herself to have her circle of friends befriend Amanda and end her budding relationship with Dan. Meanwhile, Vanessa uncovers a scandalous secret about Catherine and enlists Blair's help in using the information to help Nate; and Lily finds herself drawn to Rufus.

Serena and Dan must face their problems when they are trapped in an elevator together during a blackout. Meanwhile, Blair begins to question the lack of passion in her new relationship with Marcus as Chuck's passion for women is lost on everyone but Blair. Elsewhere, Nate must choose between his feelings for Vanessa and for Catherine.

Blair, excited over the fact that she is dating royalty, is unaware of Chuck's scheming to break up her and her new love interest, Marcus. Serena and Dan agree to keep their relationship problems a secret from their friends and family until they can figure out their future. Meanwhile, Nate begins to find the downside to having an affair with an older woman.

In the second season premiere, the gang heads up to the Hamptons to escape from the summer heat. There, Blair tries to make Chuck jealous by hooking up with another guy. Meanwhile, Nate finds a steamy hook-up of his own and Serena questions her relationship with Dan. Back in the Upper East Side, Dan lands a job at a library.

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. Meanwhile, Dan begins to ignore Serena while he continues his dirty tryst with Rachel Carr, who refuses an offer by Headmistress Queller to have her job back and chooses to spend her time semi-isolated in her apartment with Dan after school. Nate catches Vanessa flirting with another guy and he turns to Blair for help on what to do about it. Elsewhere, Lily and Rufus question where their relationship is going and talk casually about merging their households, but Chuck is against the idea and does everything to stop it.

With Serena's reputation on the line, Blair takes matters into her own hands in order to deal with Georgina Sparks once and for all. With Rufus constantly on her mind, Lily prepares for her wedding day, which is the Upper East Side's social event of the year. Serena finally is able to reveal all to Dan, but is her confession to little to late?

In the fallout of Georgina revealing why Serena left Manhattan for boarding school, Serena begins to fall back into her old ways. Seeing this, Blair, Nate and Chuck must put their feelings for one another aside to help Serena in her time of need. However, Serena cannot bring herself to tell Dan the truth, leading him to assume the worst about her. Meanwhile, Rufus' band is invited to play at a concert put on by Rolling Stone and assumes that Lily will not attend since it is the same night as her rehearsal dinner.

Georgina continues to turn Serena's world upside down and informs Serena that she is going to reveal damaging information, but no one is ready for what Georgina does next. Blair and Jenny, in an ongoing popularity war, release scandalous rumors about each other by way of Gossip Girl. Dan sees Jenny's new boyfriend cheating on her, but Jenny refuses to believe him. Meanwhile, Rufus asks Lily for advice as to how to control Jenny's recent behavior.

Serena's world is thrown into a tail spin when her former cohort, Georgina Sparks, returns to the Upper East Side in order to start trouble and reveal Serena's past in the process. When Dan notices Serena seems to be preoccupied, he assumes that it's due to her future brother-in-law Chuck. Meanwhile, Nate finds a new romance with Vanessa; Jenny meets a new guy, Asher Hornsby, who may be her door to permanent popularity; and Blair launches a plan to take down her rival, Nelly Yuki.

After being bumped from her position as Queen Bee, Blair reluctantly returns to school after being convinced to do so by Serena. Meanwhile, Serena deals with her own problems as she adjusts to living with Chuck, her future step-brother. Elsewhere, Jenny's desire to be one of the popular girls goes to a new extent when she does something illegal to win over her new group of friends.

Gossip Girl is sent a tip that Serena was seen buying a pregnancy test, but is she the one that's expecting? Meanwhile, Rufus decides to move on and Blair's dark secret is exposed.

Tragedy nearly strikes when the kids break into the school's swimming pool during the night and comes close to drowning. Tension between Serena and Dan is caused when a pact of secrecy is reluctantly agreed upon in the face of expulsion. Meanwhile, Chuck and Blair's affair is discovered by Vanessa, and Lily considers revealing her true feelings to Rufus.

Blair brings his boyfriend back home as he returns for Christmas. Meanwhile, both Serena and Dan plan a surprise for one another, and Blair worries what Chuck may tell Nate about her while they vacation. Also, Rufus and Alison's reconciliation hits a snag.

The Debutante Ball is coming up, which Serena does not want to attend, but her grandmother CeCe does not like the idea of that and demands that she attends. Serena of course wants Dan to be her date but again, her grandmother has something to say, and objects to Dan being her escort saying that he is in no way a suitable. Jenny tries to decide if she is to visit her mothers art opening or attend the Debutante Ball. Blair who is also attending the ball decides to go with Nate, but just as friends but Nate begins to think that Blair may already be seeing someone.

Rufus and Lily feel a bit awkward when Dan invites Serena's family for Thanksgiving dinner. Elsewhere, Nate and his parents also have an uncomfortable meal, and Blair is upset that her father won't be coming for Thanksgiving.

Blair attempts to hide her strained relationship with Nate during her 17th-birthday party. Meanwhile, Dan invites Vanessa to the party in hopes of becoming friends with Serena. Rufus is shocked to see Jenny;s mom home for a visit, and Nate's parents hopes he will make sacrifices to benefit the family.

Though being on again, off again for the past few weeks, Dan and Serena finally admit to one another that they are crazy about each other, despite their many differences. Chuck debates ways to make his father, Bart, proud. Nate confronts his father about drugs that he stumbles upon, but The Captain denies having a drug addiction. Meanwhile, Jenny uncovers a secret that her parents have been keeping and Blair is crushed when she learns that Nate accidentally kissed Jenny.

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.

Dan goes to extensive lengths to make his first date with Serena perfect. That night, Jenny is invited to Blair's sleepover where a revealing game of "Truth or Dare" is played. Meanwhile, Lily finds that Eric is missing from his rehab center and goes to Rufus, her ex-boyfriend, for help.

Blair is estatic when her mother chooses her to be the face of her clothing line. However, her joy is short-lived when Serena once again moves into the spotlight. Meanwhile, Serena and Dan deal with being from two very different worlds. Elsewhere, Nate and Chuck head out on a boys' weekend out after Ivy Week.

As the teens prepare for Ivy League college representatives to visit their campuses, Blair uncovers a secret about Serena that she has not intention of keeping. Dan sets his sights on impressing the Dartmouth representative, but he's beaten out by Nate, who has no interest in going to the school other than the pressure he gets from his father, The Captain. Meanwhile, Jenny and Serena's younger brother, Eric, hit it off, and Rufus asks Lily a favor.

Following the scandalous Kiss on the Lips party, Serena receives an icy welcome from Blair, who is well aware that she slept with her boyfriend, Nate, before going to boarding school. Serena decides to take Dan to Chuck's fundraising brunch at The Palace. Jenny goes to Blair for advice, and Blair decides that having Jenny in her group of friends may work to her advantage.

Serena Van Der Woodsen has returned from boarding school mysteriously. Although welcomed by most, her ex-best friend, Blair Waldorf, is less then pleased to see Serena, the blond beauty who everyone will be looking at. Jealousy is only the beginning of the twisted social lives these teens live.