List of Gossip Girl episodes

In the wake of the scandalous Kiss on the Lips party, Serena receives an icy cold reception from her best friend Blair, who reveals that she knows Serena slept with her boyfriend, Nate, before mysteriously running off to boarding school. As if it couldn't get any chillier, Serena decides to take Dan to arch-enemy Chuck's fundraiser 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.

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. 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, Dan.

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 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 makes elaborate plans to impress Serena on their first official date. The same night, Jenny is invited to the infamous Blair Waldorf sleepover and finds herself in a high stakes game of "truth or dare." Meanwhile, when Lily discovers that Eric (Connor Paolo) is missing from his treatment center, she finds herself seeking help from her ex-boyfriend, Rufus.

Dan is torn between two girls when his childhood friend, Vanessa, returns home and declares her feelings for him, just as he and Serena are trying to figure out what they mean to each other. At the infamous masked ball, Blair sends Nate on a scavenger hunt, but Nate is ultimately still distracted by his feelings for Serena. Although Blair makes it perfectly clear that outsiders are not welcome, a disguised Jenny and Dan sneak into the ball. Finally, Lily asks Rufus to accompany her to an Eleanor Waldorf event in order to make Bart Bass jealous.

After surviving the on-again/off-again nature of their new relationship, 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, The 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.

Devastated by the current state of her relationship with Nate and still dealing with the guilt from her recent indiscretion, Blair puts on a happy face for her 17th birthday party and attempts to hide the truth from her friends. Hoping to ease the tension between Serena and Vanessa, Dan takes Vanessa to Blair's party so the girls can have some bonding time, but this only ends up making Serena more uncomfortable. Jenny brings her mom home for a surprise visit, but Rufus may not be ready to forgive and forget. Nate's parents ask him to make a huge sacrifice in an effort to salvage his father's business as he faces charges of embezzlement and fraud.

When Dan hears that Serena and her family are spending Thanksgiving alone at The Palace, he naively invites them to spend the holiday with his family, creating an uncomfortable situation for Rufus and Lily whose children are unaware of their complicated romantic history. Meanwhile, Blair's emotions spiral out of control when she learns that her father isn't coming home for Thanksgiving. Nate spends the holiday with his mom and dad, but their awkward dinner quickly goes from bad to worse.

Serena’s plan on not attending the annual Cotillion Ball is sidetracked when her grandmother CeCe persuades her to attend; Nate sees Blair’s new buoyant attitude and entrusts Chuck to find out the reason, in which he tells him that she is having an affair with St. Jude’s alumni Carter Baizen, creating drama at the Ball. Blair finds out Chuck did this for personal gain and ends their affair, returning to Nate once more and consummating her love to him during a passionate night. Meanwhile, Jenny attends the ball despite it being on the same night as Alison’s art gallery opening.

When Blair's father, Harold, comes home for the holidays with an unexpected guest -- his boyfriend, Roman -- Blair finds it difficult to hide her disappointment and hatches a plan to get rid of Roman for good. 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 texts Blair that Nate has joined him in Monaco, worrying Blair that Chuck may disclose the details of their hook-up. Rufus refuses to remain the understanding husband any longer after Alison's former lover calls the house.

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, and this time is no exception. Later it is revealed that Serena bought the pregnancy tests for Blair, who is unsure of who the father would be - Chuck or Nate. Chuck's jealously over Nate and Blair's reconciliation pushes him to reveal a few home truths to Gossip Girl and knock Queen B off her throne and end his bromance with Nate.

Having been recently dethroned as Queen Bee in the last episode by Gossip Girl, with an assist from scheming "little J", Blair hesitantly returns to school with the support of her BFF, Serena. Meanwhile, Serena struggles to adjust to her new living arrangements with her future step-brother, Chuck, while receiving disturbing packages from an unknown sender. Jenny's drive to be popular hits an all-new time high when she does something illegal to fit in with her new Upper East Side friends.

Serena's Upper East Side world is turned upside down when her former partner in all things bad, Georgina Sparks, returns to Manhattan to stir up trouble and Serena's past. When Dan notices that Serena seems preoccupied he jumps to the conclusion that it must have something to do with Serena's new roomie and soon-to-be step-brother, Chuck. Nate finds romance with the last person he was expecting to connect with, Vanessa. Jenny meets a new guy, Asher Hornsby, who just might be her ticket to permanent popularity. Finally, Blair hatches a secret plan to sabotage her biggest rival, Nelly Yuki.

Georgina informs Serena that she is prepared to reveal damaging information from Serena's past, but no one is prepared for what Georgina does next. Blair and Jenny escalate their "popularity war" by spreading scandalous rumors about each other through Gossip Girl. Dan witnesses Jenny's new boyfriend, Asher, cheating on her, but Jenny refuses to listen to her brother's warning. Rufus goes to Lily for advice on how to handle Jenny's recent out-of-character behavior.

As a result of Georgina revealing the true reason that Serena fled Manhattan for boarding school, Serena falls back into her old habits and Blair, Nate and Chuck must put their complicated feelings for each other aside to help their friend. Unfortunately, Serena is too ashamed to share the truth with Dan, leaving him only to assume the worse about his girlfriend. Rufus is thrilled 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.

With her best friend Serena's life and reputation on the line, Blair decides to take matters into her own hands in dealing with the manipulative and evil Georgina. With Rufus never far from her thoughts, Lily prepares for her wedding day which is destined to be the Upper East Side's social event of the year. Serena finally pours out her heart and the truth about her past to Dan, but will it prove to be too late to save their relationship?

As the summer draws to a close in the Hamptons, Serena and Nate have everyone fooled into thinking they are a couple to cover up the fact that Nate has been hooking up with an older, married woman named Catherine (guest star Madchen Amick). Blair returns from abroad with a hot guy on her arm (guest star Patrick Heusinger), making a very jealous Chuck (Ed Westwick) question his decision to leave Blair stranded at the heliport. Dan has spent the summer assisting a famous author (guest star Jay McInerney), and clearly still has one certain girl on his mind, which results in him going after her. While interning for Eleanor Waldorf's company, Jenny sneaks an invite to a much-coveted Hamptons' White Party at which Eric introduces her to socialite Tinsley Mortimer.

Blair is over the moon that she is dating royalty and has every intention of becoming a royal herself, but a scheming Chuck has other plans for Blair and her new love. Meanwhile, Nate learns the downside to having an affair with Catherine when he keeps getting caught in his lies and learns his family has gone bankrupt due to his father jumping bail. Dan and Serena deal with their new found relationship. Serena wants time to figure out what this all means for the two, but she just cannot get Dan out of her thoughts.

In a humorous twist, Blair questions the lack of passion in her relationship with Marcus, while at the same time Chuck appears to have lost his "passion" for any woman other than Blair. Meanwhile, Nate struggles between his feelings for Vanessa and his more-complicated-by-the-day relationship with Catherine. Jenny risks losing her internship when Eleanor catches Jenny critiquing one of the Eleanor Waldorf designs. Whilst being stuck in a elevator due to the blackout, Dan and Serena talk about their relationship and come to the conclusion that they are totally two different people and that it won't work out for the two.

Blair and her minions decide to befriend the new girl Amanda (guest star Laura-Leigh) in order to sabotage her. Vanessa discovers a scandalous secret about Catherine and enlists Blair's scheming expertise to use the information to help Nate. Meanwhile, Lily finds herself drawn back to her ex, Rufus, once again.

In the midst of Fashion Week, a furious Blair learns that her mother, Eleanor, at the suggestion of her protege Jenny, has given Serena and her new socialite friend, Poppy Lifton (guest star Tamara Feldman), front row seats to the Eleanor Waldorf show. Hurt once again by Serena's popularity and her mother's betrayal, Blair decides to sabotage the show. Meanwhile, Dan starts hanging out with Chuck, but a walk on the dark side always has its risks and Dan learns that the hard way. Lily learns a secret that her new husband Bart has been keeping from her.

After Blair and Serena 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 frantically tries to figure out a way to salvage his chances of getting into the school. While on the Yale campus, Chuck is kidnapped by a group of Skull and Bones members and Nate hooks up with a co-ed.

Vanessa uses the scandalous picture of Catherine and Marcus to blackmail Blair into being a nicer person, so Blair seeks revenge by enticing Chuck to seduce Vanessa. Lily and Bart throw an extravagant housewarming party and expect their children to make them proud in front of the attending press, but a rebellious Serena isn't ready to play by their rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.

Jenny befriends a young model, Agnes (guest star Willa Holland), who encourages Jenny to not only explore her wild side, but also confront her boss, Eleanor Waldorf, who is attempting to "borrow" Jenny's designs. Serena meets an artist, Aaron Rose (guest star John Patrick Amedori), and realizes they have an instant chemistry. Blair attempts to seduce Chuck, but it proves tougher than she ever imagined.

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 the 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.

Blair does not approve of the new man, Cyrus Rose (guest star Wallace Shawn), in her mother's life, so she makes it her mission to break up the lovebirds by any means necessary. Jenny moves in with Agnes as the friends move forward with their plans for a fashion line. Serena continues to fall for the new guy in her life, Aaron, but she learns something about him that threatens to end things just as they are getting really good. Dan decides to win the trust of Bart Bass in order to learn more about the man and possibly write an expose on him for Vanity Fair, but things get heated after Chuck finds out the real reason Dan is spending so much time around his family.

Thanksgiving in the Waldorf household finds Blair upset that her mom's new boyfriend, Cyrus, has decided to ruin all her favorite traditions, but that's nothing compared to what's coming next. Lily finds herself trying to broker a peace treaty between Rufus and Jenny who is prepared to cut off all communication with her father if she doesn't get her way. Serena isn't quite ready to come clean with Aaron about her complicated past, but Dan ends up accidentally revealing a few tidbits of his own. Vanessa and Chuck come to their friend's aid when Nate is once again forced to confront his father's abandonment. Finally, Eric discovers a secret that Bart has been keeping from Lily.

For the annual Snowflake Ball, Blair and Chuck make a bet that they can find the ideal dates for each other. Aaron's ex-girlfriend, Lexi (guest star Natalie Knepp), expresses an interest in Dan. Nate, Jenny and Vanessa get into a tangled situation that puts their friendships and hearts on the line.

A sudden and tragic event impacts the lives of our favorite Upper East Side teens and their parents. Aaron ask's Serena to come with him on a holiday to Argentina, at first she's reluctant to agree, but after a conversation with Dan, she accepts Aaron's offer and goes with him. Dan tries to stop Serena after he realises he wants to be with her, but she explains that she believes their parents will soon become an item and that she will not stand in her mother's away a second time.

With Chuck MIA since his father's funeral, Jack (guest star Desmond Harrington) 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. Dan and Serena meet in the hallway at the school and she immediately tells him that her and Aaron broke up 3 hours into their 15 hour flight, she explains she never called him because she wanted to wait for the dust to settle and wanted to know if he still felt the same, Dan responds with a kiss.

With the reading of Bart's will, Chuck, Bart's brother, Jack, and Blair learn the fate of the Bass empire. Rufus and Lily's 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 does some investigating and uncovers Rufus and Lily's secret, putting him in the awkward situation of deciding what to do with this shocking revelation and who to share it with.

It's that stressful time of year when Constance Billard and St. Jude's students find out who is and isn't worthy of early admission to Yale University. Serena bonds with her new Shakespeare teacher, Rachel (guest star Laura Breckenridge), who has no clue the wrath she is about to suffer after giving Blair the first B of her prep school career. Chuck pairs up with an unlikely ally in his war with Jack over Bass Industries.

In retaliation for not playing by the unspoken rules of Constance Billard, Blair hatches a plan to bring down her teacher, Rachel, and it's going to be good. After Chuck wakes up in a hotel and only has a minor recollection of what happened the previous evening and who he spent the evening with, Nate and Vanessa tries to help him fill in the missing pieces of what is turning out to be an increasingly intriguing mystery.

The Constance Billard and St. Jude seniors put on a production of The Age of Innocence and find their personal lives mirroring conflicts in the play. Serena develops a crush on the play's director, Julian (guest star Harmon Walsh), and enlists Vanessa's knowledge of theater to help her get the otherwise uninterested guy's attention. Blair receives devastating news about her future that leads her on a witch-hunt for the person responsible. Dan and Rachel agree to stay away from each other in the aftermath of being discovered as more than teacher and student, but find it impossible to keep that promise. Chuck enlists help from an unlikely source, his nemesis Carter Baizen (guest star Sebastian Stan).

Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf existence in favor of a more wild and unpredictable lifestyle, 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 van der Bilts, who abandoned Nate and his mother when they needed them most. In a misguided effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers.

Serena decides to throw Jenny an intimate party for her sixteenth birthday, but things get way out of control when Poppy Lifton (guest star Tamara Feldman) turns the small gathering into a huge social event. In a moment of weakness, Vanessa agrees to help Chuck with a scheme having to do with Blair and Nate. 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.

Serena returns from her trip to Spain with Poppy and Gabriel (guest star Armie Hammer). Blair makes a secret deal with Nate's grandfather, William (guest star James Naughton), and Nate learns some disturbing information about his father's arrest. Dan takes a job as a cater-waiter to earn money for college, but is distressed when he discovers the gig is a Passover seder at the Waldorf penthouse and several of his friends and family are guests.

Georgina Sparks returns to the Upper East Side after undergoing a major transformation. 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.

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.

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".

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 challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year. Lily and Rufus 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. Nate decides to go on the backpacking trip with Vanessa, while Georgina recovers Dan's money and requests Blair for a roommate at NYU. Carter Baizen reveals to Serena where her father is. In the end Serena is going to Brown, Blair, Dan, Vanessa, and Georgina are going to NYU, and Nate is going to Columbia.

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. Chuck and Blair play a game where Chuck pretends to be interested in other girls to have Blair humiliate them, showing that she's Chuck's girlfriend. Serena returns from her European adventure back to her old partying ways and has a complicated relationship with Carter Baizen (guest star Sebastian Stan). Nate returns from his travels with a mysterious brunette, Bree Buckley (guest star Joanna Garcia) 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.

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. Georgina hosts a party that loads of people come to, but Blair invites Georgina's Christian friends from Bible Camp who turn it into a conversion party. Blair then invites everyone to her party, but Dan convinces them to stay. 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. Serena and Carter turn up at a bar where Chuck is doing a business deal and ruin it. Carter realizes Serena is using him to get back at Chuck and leaves. Nate and Bree decide to explore their relationship further, knowing full well that it could cause tension between their families who are political rivals. Bree thinks if she and Nate had a proper relationship they would break up, but changes her mind. In the end, Dan takes an interest in Georgina. In this episode, Leighton Meester's duet with Cobra Starship 'Good Girls Go Bad' is featured.

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. Blair needs the painting to be accepted into a prestigious society and Chuck needs the painting to impress a man he is trying to make a deal with. With their constant bickering over the painting, Serena decides to buy the painting herself. Serena suspects that Carter may be up to his old habits again, Georgina takes an interest in Dan, and Vanessa begins to suspect that something isn't quite right with Scott. Old hatred arouses between S and G again. Blair decides to give the painting to Chuck, seeing that she loves and believes in him. Chuck later buys a hotel at the end of the episode.

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. Lily returns home to Rufus and her family to find that things are definitely not as she left them. A famous movie actress, Olivia Burke (Hilary Duff), enrolls at NYU – and is assigned to be Vanessa’s roommate – hoping for a somewhat normal college experience. Tyra Banks guest stars as Ursula, an actress co-starring in Olivia’s movie and someone who Serena befriends. Deanna Russo also makes an appearance as K.C. Cunningham the Publicist of Olivia and Ursula. Musicians HelenaMaria appear at the end of the episode as two of Blair's subservient underlings.

Lily and Rufus 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 discovers a secret that Carter has been keeping from Serena. Dan and Vanessa are pulled into one of Georgina’s schemes. Blair is suspicious of Bree and shares her concerns with Nate. Lily freaks out about committing and her and Rufus argue. Scott interrupts and Lily tells him to go away. Georgina says Scott is their long lost son and Vanessa and Dan confirm it. Lily and Rufus chase after Scott and stop him getting the bus back to Brooklyn. Carter reveals to Serena it was he who abandoned Bree's cousin at the alter, and Serena feels she can no longer trust him. Chuck tells Bree that Carter is accompanying Serena to the wedding, so she brings some of her cousins to pin him down. Chuck warns Carter about this, but Carter shows up anyway to talk to Serena. Sonic Youth performs "Star Power" at the wedding reception.

Vanessa, hoping to finally win her mother Gabriela’s (guest star Gina Torres) approval, desperately vies with Blair for the honor of delivering the freshman toast at NYU, so blackmails the head of Freshman affairs into giving it to her by setting Chuck up to kiss him. Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple since Vanessa told Olivia they hated celebrities. Olivia then acts snobbishly. Vanessa, angry about not giving the toast, takes a microphone and puts it in her purse. She records Blair saying why she is better than her, and how she used Chuck. Blair's rant is played on the speakers, and Chuck hears, and walks out. Serena and Nate team up to help Carter.

It's Halloween on The Upper East Side and 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, but tells her not to tell Blair. Feeling left out of the planning, Blair attempts to win Chuck’s approval by secretly helping him with his liquor license by phoning Jack Bass. Dan is unnerved when he finally watches one of Olivia’s (Hilary Duff) infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson (guest star Simon Miller). Jenny is forced to choose between her relationship with Eric and her new role as Queen Bee. When he sits higher than her on the met steps her minions pour almond yogurt on him. While Jenny and Eric are at Chuck's clubs opening she gets her friends to egg Johnathan. Meanwhile Rufus gets Lily into the Halloween spirit, but Lily has some plans of her own. Chuck and Blair find out the liquor license was fake, and so call the cops.

Olivia says something she regrets during her appearance on Jimmy Fallon’s (Fallon playing himself) talk show and tries to keep Dan from finding out. With election day around the corner, Nate and Vanessa suspects that William will stop at nothing to get Tripp (guest star Aaron Tveit) elected to congress. In the midst of another feud with Serena, Blair befriends who she believes to be the new “it” girl and takes her to Tripp's election party, hoping to make Serena jealous. Vanessa becomes upset with Nate because of his schemes during the election.

Jenny is desperate to shed her Brooklyn past as she feels obligated to fulfill her role in becoming queen of the Upper East side—regardless of compromising friendships and morals. Eric and Jonathan end their relationship due to Eric's change in character. Dan and Vanessa attempt to accomplish a list of college experiences (including a threesome) in hopes that Olivia (Hilary Duff) doesn't leave NYU for a new movie. Olivia receives a text that the movie has been canceled as the three lay in bed together. Blair and Serena's friendship is repaired as Serena confesses she had sought out her estranged father, and failed doing so. Serena and Tripp may become more than just friends.

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. Dan and Olivia (Hilary Duff) 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 her crush on Tripp. As a favor to Chuck, Jenny 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. He is a drug dealer, and he gives her some E, but Chuck stops her before she takes it. Nate tells Serena that he loved her, but Tripp walks in as they are about to kiss.

It wouldn’t be Thanksgiving on the Upper East Side if there wasn’t a serving or two of some major drama for the holiday. Blair suspects her mom has been keeping a big secret from her, but it turns out to be something else entirely. Vanessa is supposed to spend Thanksgiving with her parents, but has a fight with her mom and shows up on Dan’s doorstep. Rufus learns that Lily has been lying to him about her mother, Cece. Chuck tells Nate that he has some potentially damaging information about one of their friends. Jenny learns that Eric was behind her very public embarrassment at Cotillion and can’t pass up a chance to get even. Serena is put in a very awkward position when her mother invites Tripp and Maureen to join them for Thanksgiving dinner.

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.

Title comes from the 2006 movie The Departed.

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