Pilot
Season 1, Episode 1 Unrated
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The privileged prep school teens on Manhattan's Upper East Side first learn that Serena van der Woodsen (Blake Lively, "The Sisterhood of the Traveling Pants") is back in town the way they learn all the important news in their lives -- from the blog of the all-knowing albeit ultra- secretive Gossip Girl. No one knows Gossip Girl's identity, but everyone in this exclusive and complicated vicious circle relies on her website and text messages for the latest scoop. Even Serena's closest friend, Blair Waldorf (Leighton Meester, "Entourage"), is surprised to find that Serena has suddenly ended her self-imposed exile to boarding school and returned to Manhattan. Once the Upper East Side's most notorious party girl, Serena's reasons for returning are mysterious, although they may have something to do with her younger brother Eric (Connor Paolo, "Alexander"). Whatever the reasons, the change in Serena is obvious, especially to Blair, whose friendship with Serena has always been competitive and difficult.
The Wild Brunch
Season 1, Episode 2 Unrated
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In the wake of the scandalous Kiss on the Lips party, Serena receives an ice-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. Serena decides to take Dan to archenemy 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.
Poison Ivy
Season 1, Episode 3 Unrated
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As the Upper East Side teens from Constance Billard and St. Jude's prepare for a much-anticipated visit from Ivy League representatives, Blair uncovers scandalous information about Serena that may not remain a secret much longer. Dan has his heart -- and future -- set on serving in the coveted usher position for the Dartmouth representative. But he is beat out by Nate, who has no interest in the school, despite pressure from his controlling father, the Captain (recurring guest star SAM ROBARDS). Meanwhile, Jenny bonds with Serena's younger brother, Eric (recurring guest star CONNOR PAOLO). And Rufus must swallow his pride and ask Lily for a favor to help his son, Dan.
Bad News Blair
Season 1, Episode 4 Unrated
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Blair is thrilled when her mother 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.
Dare Devil
Season 1, Episode 5 Unrated
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Dan makes elaborate plans to impress Serena on their first official date. On 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 (recurring guest star CONNOR PAOLO) is missing from his treatment center, she seeks help from her ex- boyfriend, Rufus.
The Handmaiden's Tale
Season 1, Episode 6 Unrated
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Dan is torn between two girls when his childhood friend, Vanessa (recurring guest star JESSICA SZOHR), 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 her infamous masked ball, Blair sends Nate on a scavenger hunt, but he is 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. Meanwhile, Lily asks Rufus to accompany her to an event hosted by Blair's mother in order to make Chuck's father, who brought a model ("America's Next Top Model" winner CARIDEE ENGLISH) as his date, jealous.
Victor/Victrola
Season 1, Episode 7 Unrated
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After surviving their relationship's on-again/off-again genesis, Serena and Dan finally acknowledge that 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, hoping to make his hard-to-please father, Bart (recurring guest star ROBERT JOHN BURKE), proud of him. Nate confronts his father, the Captain (recurring guest star SAM ROBARDS), about the drugs he found in the house, but the Captain denies having a problem. Jenny discovers a secret that her father, Rufus, and mother, Alison (SUSAN MISNER), have been keeping from her. And Blair is once again devastated by Nate's actions after Jenny reveals that Nate accidentally kissed her, thinking she was Serena.
Seventeen Candles
Season 1, Episode 8 Unrated
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Devastated by the state of her relationship with Nate and still dealing with the guilt from a 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 (recurring guest star JESSICA SZOHR), Dan takes Vanessa to Blair's party so the girls can have some bonding time, but this only ends up making Serena more uncomfortable. Meanwhile, Jenny brings her mom (recurring guest star SUSAN MISNER) home for a surprise visit, but Rufus may not be ready to forgive and forget. And Nate's parents ask him to make a huge sacrifice in order to salvage the business of his father, who faces charges of embezzlement and fraud.
Blair Waldorf Must Pie
Season 1, Episode 9 Unrated
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When Dan finds out that Serena and her family are celebrating Thanksgiving alone, he naïvely 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 marks the holiday with his mom and dad, but their awkward dinner quickly goes from bad to worse.
Hi, Society
Season 1, Episode 10 Unrated
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Serena has absolutely no intention of attending the upcoming Debutante Ball, until her grandmother, CeCe (guest star CAROLINE LAGERFELT - "All the King's Men," "Nash Bridges"), announces that Serena must attend. Unfortunately, CeCe does not find Dan to be the "suitable escort" she had in mind for Serena, and makes her opinion heard loud and clear, causing a riff between Serena and Dan. Blair and Nate, now officially broken up, decide to go to the ball together as friends; however, Nate becomes jealous when he begins to suspect that Blair may already be seeing someone else. Meanwhile, Jenny finds herself torn between attending her mother’s (recurring guest star SUSAN MISNER) art opening or following her dreams of going to the Debutante Ball, even though the latter is against her parents’ wishes. And Rufus finally learns the real reason Lily broke up with him all those years ago.
Roman Holiday
Season 1, Episode 11 Unrated
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When Blair’s father, Harold (recurring guest star JOHN SHEA), comes home for the holidays with an unexpected guest -- his boyfriend, Roman (guest star WILLIAM ABADIE - "Entourage," "The O.C.," "The Pink Panther") -- Blair finds it difficult to hide her disappointment and hatches a plan to get rid of Roman for good. Meanwhile, Jenny and Vanessa (recurring guest star JESSICA SZOHR) help Serena plan the best Christmas surprise ever for Dan; Dan, in turn, may be thinking of his own surprise for Serena. And when Chuck texts Blair from Monaco saying that Nate has joined him there, Blair worries that Chuck may disclose the details of their hook-up. Back in Brooklyn, Rufus refuses to remain the understanding husband after a former lover of Alison's (recurring guest star SUSAN MISNER) calls the house.
School Lies
Season 1, Episode 12 Unrated
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The gang breaks into the school swimming pool for an impromptu 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 risk his future and take the fall for someone else. Meanwhile, Vanessa (recurring guest star JESSICA SZOHR), who is working on a documentary project about private schools, accidentally captures Blair and Chuck discussing their affair, and Lily contemplates telling Rufus how she really feels about him.
The Thin Line Between Chuck and Nate
Season 1, Episode 13 Unrated
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Gossip Girl takes pleasure in reporting that Serena van der Woodsen has been spotted buying a pregnancy test, and the word spreads like wildfire. Of course, on the Upper East Side, the truth is often juicier and more scandalous than the gossip, and this time is no exception.
The Blair Bitch Project
Season 1, Episode 14 Unrated
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Having recently been 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 stepbrother, Chuck, while receiving disturbing packages from an unknown sender. And Jenny's drive to be popular hits a new all-time high when she does something illegal to fit in with her new Upper East Side friends.
Desperately Seeking Serena
Season 1, Episode 15 Unrated
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Serena's Upper East Side world is turned upside down when her former partner in all things bad, Georgina Sparks (recurring guest star MICHELLE TRACHTENBERG - "Buffy the Vampire Slayer," "Six Feet Under"), 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 roommate and soon-to-be stepbrother, Chuck. Meanwhile, Nate finds romance with the last person he was expecting to connect with, Vanessa, and Jenny meets a new guy, Asher Hornsby (recurring guest star JESSE SWENSON), who just might be her ticket to permanent popularity. Plus, Blair hatches a secret plan to sabotage her biggest rival, Nelly Yuki (guest star YIN CHANG - "Law & Order: Criminal Intent," "Six Degrees").
All About My Brother
Season 1, Episode 16 Unrated
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Georgina (recurring guest star MICHELLE TRACHTENBERG) informs Serena that she is prepared to reveal damaging information from Serena's past, but no one is ready 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 (recurring guest star JESSE SWENSON), 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. Plus, one of the Upper East Side teens reveals that he is gay.
Woman on the Verge
Season 1, Episode 17 Unrated
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Georgina (recurring guest star MICHELLE TRACHTENBERG) reveals the true reason that Serena fled Manhattan for boarding school, and Serena quickly falls back into her old habits. 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 to assume the worst about his girlfriend. Meanwhile, Rufus is thrilled when his band is invited to perform at a Rolling Stone-sponsored concert, but Lily is the last person he expects to see at the performance, especially since her wedding rehearsal dinner is the same night. Recording artist LISA LOEB and famous cake designer SYLVIA WEINSTOCK appear as themselves.
Much 'I Do' About Nothing
Season 1, Episode 18 Unrated
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With Serena's life and reputation on the line, Blair -- as Serena's best friend -- decides to take matters into her own hands to deal with the manipulative and evil Georgina Sparks (recurring guest star MICHELLE TRACHTENBERG). Lily prepares for her wedding day, which is destined to be the Upper East Side's social event of the year, and finds that Rufus is never far from her thoughts. Serena finally opens up to Dan, pours out her heart and tells him the truth about her past, but will it prove to be too late to save their relationship? And Lily's interior decorator, Amelia (heiress and model LYDIA HEARST), makes a big impression on Chuck.
Summer, Kind of Wonderful
Season 1, Episode 19 Unrated
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Gossip Girl heads to the Hamptons as summer comes to a close. Guest stars include author JAY McINERNEY (Bright Lights, Big City), socialite TINSLEY MORTIMER and MADCHEN AMICK.
Never Been Marcused
Season 1, Episode 20 Unrated
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Blair is over the moon to be dating royalty and has every intention of becoming a royal herself, but a scheming Chuck has other plans for Blair and her new love, Marcus (recurring guest star PATRICK HEUSINGER). Serena and Dan agree to keep their recent hookups a secret from their friends and family until they figure out what it means for their relationship. Meanwhile, Nate learns the downside to having an affair with a hot older woman, Catherine (recurring guest star MADCHEN AMICK), who is married.
The Dark Night
Season 1, Episode 21 Unrated
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Serena and Dan are forced to deal with their unspoken problems while trapped in an elevator during a citywide blackout. In a humorous twist, Blair questions the lack of passion in her relationship with Marcus (recurring guest star PATRICK HEUSINGER), 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 (recurring guest star MADCHEN AMICK). Plus, Jenny risks losing her internship when Eleanor (recurring guest star MARGARET COLIN) catches Jenny critiquing one of the Eleanor Waldorf designs.
The Ex-Files
Season 1, Episode 22 Unrated
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When Serena notices that Dan has been cozying up to the new girl in school, Amanda (guest star LAURA-LEIGH), the ever-loyal Blair and her minions decide to befriend Amanda and sabotage her budding new romance with "lonely boy." Plus, Vanessa discovers a scandalous secret about Catherine (recurring guest star MADCHEN AMICK) 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.
The Serena Also Rises
Season 1, Episode 23 Unrated
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Blair decides to sabotage her mother's show at Fashion Week. Dan starts hanging out with Chuck, and learns the hard way that a walk on the dark side always has its risks. Designer MICHAEL KORS and socialites TINSLEY MORTIMER and CRISTINA CUOMO make cameo appearances at Eleanor Waldorf's show.
New Haven Can Wait
Season 1, Episode 24 Unrated
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After a fight, Serena wants to get even with Blair -- who dreams of attending Yale University -- and accepts an invitation to visit. Chuck is kidnapped by an elite secret society.
Chuck in Real Life
Season 1, Episode 25 Unrated
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Blair seeks revenge by enticing Chuck to seduce Vanessa. Serena rebels at an important party of Lily's. And Dan and Jenny find out a secret Nate has been hiding from his friends.
Pret-A-Poor J
Season 1, Episode 26 Unrated
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Jenny befriends a model (WILLA HOLLAND - "The O.C."), and is encouraged to explore her wild side. Serena is attracted to an artist, Aaron Rose (JOHN PATRICK AMEDORI - "Vanished").
There Might Be Blood
Season 1, Episode 27 Unrated
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Serena realizes Aaron (JOHN PATRICK AMEDORI) has kept a secret from her. Jenny and Agnes (WILLA HOLLAND) plan a guerilla fashion show. Blair babysits the daughter of a Yale donor.
Bonfire of the Vanity
Season 1, Episode 28 Unrated
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Dan tries to get close to Bart Bass (recurring guest star ROBERT JOHN BURKE) to possibly write an exposé, but things get heated when Chuck finds out. WALLACE SHAWN guest stars.
The Magnificent Archibalds
Season 1, Episode 29 Unrated
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Blair's favorite Thanksgiving traditions are ruined by her mother's new boyfriend (WALLACE SHAWN). Serena doesn't tell Aaron (JOHN PATRICK AMEDORI) about her past -- but Dan does.
It's a Wonderful Lie
Season 1, Episode 30 Unrated
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At the annual Snowflake Ball, Blair and Chuck bet they can find ideal dates for each other. Aaron's (JOHN PATRICK AMEDORI) ex-girlfriend (NATALIE KNEPP) shows interest in Dan.
O Brother, Where Bart Thou?
Season 1, Episode 31 Unrated
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A sudden and tragic event impacts the lives of everyone.
In the Realm of the Basses
Season 1, Episode 32 Unrated
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Chuck's uncle, Jack Bass (recurring guest star DESMOND HARRINGTON - "Dexter," "Rescue Me") arrives on the scene. Meanwhile, Jenny returns to school and takes on the mean girls.
Gone With the Will
Season 1, Episode 33 Unrated
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Bart's will is read and everyone learns the fate of the Bass empire. Plus, Dan discovers the secret between Rufus and Lily, and must decide what to do with the information.
You've Got Yale!
Season 1, Episode 34 Unrated
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Which students will be accepted to Yale University? Plus, Chuck pairs up with an unlikely ally in his war with Jack (recurring guest star DESMOND HARRINGTON) over Bass Industries.
Carnal Knowledge
Season 1, Episode 35 Unrated
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Blair comes up with a plan to get revenge on her teacher, Rachel (LAURA BRECKENRIDGE). Chuck wakes up in a hotel and tries to piece together what happened the night before.
The Age of Dissonance
Season 1, Episode 36 Unrated
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The seniors put on a production of "The Age of Innocence." Chuck enlists help from an unlikely source -- his nemesis, Carter Baizen (SEBASTIAN STAN - "Kings," "The Covenant").
The Grandfather
Season 1, Episode 37 Unrated
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Devastated by the recent plot twist in her life, Blair turns her back on her predictable existence in favor of a wilder lifestyle, causing Serena and Chuck to be concerned.
The Remains of the J
Season 1, Episode 38 Unrated
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Serena throws Jenny a party for her 16th birthday, but things get way out of control when Poppy Lifton (TAMARA FELDMAN) turns the small gathering into a huge social event.
Seder Anything
Season 1, Episode 39 Unrated
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Serena returns from her trip to Spain with Poppy (recurring guest star TAMARA FELDMAN) and Gabriel (recurring guest star ARMIE HAMMER). Blair makes a secret deal with Nate's grandfather, William (recurring guest star JAMES NAUGHTON - "The Devil Wears Prada"), and Nate learns some disturbing information about his father's arrest. Meanwhile, 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, where several of his friends and family will be guests.
Southern Gentleman Prefer Blondes
Season 1, Episode 40 Unrated
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Georgina (recurring guest star MICHELLE TRACHTENBERG) returns to the Upper East Side after undergoing a major transformation. Chuck and Nate find themselves at a major crossroads in their friendship, a result of their mutual interest in Blair. And Serena finds her relationship with Gabriel (recurring guest star ARMIE HAMMER) growing more complicated.
The Wrath of Con
Season 1, Episode 41 Unrated
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Blair pressures Georgina (recurring guest star MICHELLE TRACHTENBERG) to help her in a scheme to make amends for her past bad behavior. The rivalry between Nate and Chuck over Blair comes to a head. And Lily hatches a secret plan to help Rufus with Dan's college tuition.
Valley Girls
Season 1, Episode 42 Unrated
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In a special flashback to the 1980s, before she became Lily van der Woodsen, 17-year-old Lily Rhodes (guest star BRITTANY SNOW - "American Dreams," "Hairpray") is kicked out of boarding school and runs away to Los Angeles to reconnect with her parents, Rick (guest star ANDREW McCARTHY - "Lipstick Jungle," "Pretty in Pink") and CeCe (guest star CYNTHIA WATROS - "Lost"), and her older sister, Carol (guest star KRYSTEN RITTER - "Confessions of a Shopaholic"). Plus, NO DOUBT performs as an eighties band called Snowed Out. Back in present day New York City, Blair and Nate attend the prom together, but the evening doesn't turn out exactly as planned -- something Chuck may have a little to do with. And Serena and Lily don't see eye to eye over Serena's recent run-in with the law. Recurring guest star MICHELLE TRACHTENBERG appears as Georgina.
The Goodbye Gossip Girl
Season 1, Episode 43 Unrated
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At the Constance Billard and St. Jude graduations, Gossip Girl livens things up 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 (recurring guest stars YIN CHANG, NICOLE FISCELLA, AMANDA SETTON and DREAMA WALKER) challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year, and Lily and Rufus struggle to repair their relationship after Lily's betrayal. Plus, the season finale is rife with cliffhangers: Blair and Chuck finally … Serena is shocked by … Georgina (recurring guest star MICHELLE TRACHTENBERG) decides to … And Dan, Nate and Vanessa unknowingly …. OMG!
Reversals of Fortune
Season 1, Episode 44 Unrated
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As the summer draws to a close, Blair (series star LEIGHTON MEESTER) and Chuck (series star ED WESTWICK) are madly in love and adjusting to their new "in a relationship" status, though breaking all traditional rules of dating, as would be expected. Serena (series star BLAKE LIVELY) returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen (recurring guest star SEBASTIAN STAN - Kings). Nate (series star CHACE CRAWFORD) returns from his travels with a mysterious brunette, Bree Buckley (recurring guest star JoANNA GARCIA - Privileged, Reba) in tow. Rufus (series star MATTHEW SETTLE), Dan (series star PENN BADGLEY) and Jenny (series star TAYLOR MOMSEN) spent the summer in the Hamptons, adjusting to the van der Woodsen's glamorous lifestyle surprisingly faster than any of them expected. The series also stars JESSICA SZOHR as Vanessa and KELLY RUTHERFORD as Lily van der Woodsen Bass.
The Freshman
Season 1, Episode 45 Unrated
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Blair, determined to maintain her Queen Bee status in college, embarks on her first day at NYU, along with Dan and Vanessa. Unfortunately, Georgina (recurring guest star MICHELLE TRACHTENBERG) turns up as Blair's roommate in the dorms, determined to make Blair a social outcast. As Serena prepares to depart for Brown, she and Chuck have a major falling out, so she recruits Chuck's enemy, Carter (recurring guest star SEBASTIAN STAN), to help her get even. Meanwhile, Nate and Bree (recurring guest star JoANNA GARCIA) decide to explore their relationship further, knowing full well it could cause tension between their families who are political rivals.
The Lost Boy
Season 1, Episode 46 Unrated
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It's a bidding war on the Upper East Side. Blair and Chuck both set their sights on a particular item up for bid at Sotheby's, and the personal stakes are high. Plus, Serena suspects that Carter (recurring guest star SEBASTIAN STAN) may be up to his old habits, Georgina (recurring guest star MICHELLE TRACHTENBERG) takes an interest in Dan and Vanessa begins to suspect that something isn't quite right with Scott (recurring guest star CHRIS RIGGI - "Lipstick Jungle," "Dare").
Dan de Fleurette
Season 1, Episode 47 Unrated
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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.
Rufus Getting Married
Season 1, Episode 48 Unrated
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Lily and Rufus decide to move up their wedding to the next day, but will someone or something come between them before they can become married? Chuck discovers a secret that Carter (recurring guest star SEBASTIAN STAN) has been keeping from Serena. Dan and Vanessa are pulled into one of Georgina's (recurring guest star MICHELLE TRACHTENBERG) schemes. Blair is suspect of Bree (recurring guest star JoANNA GARCIA) and shares her concerns with Nate. Musical group SONIC YOUTH performs.
Enough About Eve
Season 1, Episode 49 Unrated
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Vanessa, hoping to finally win the approval of her mother, Gabriela (guest star GINA TORRES - 24, Alias, Firefly), desperately vies with Blair for the honor of delivering the freshman toast at NYU, but at what price? Dan invites Olivia (recurring guest star HILARY DUFF) to meet Rufus and Lily, which leads to all sorts of problems for the new couple. Serena and Nate team up to help Carter Baizen (recurring guest star SEBASTIAN STAN).
How to Succeed in Bassness
Season 1, Episode 50 Unrated
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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 (recurring guest star HILARY DUFF) infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson (recurring guest star SIMON MILLER - Elah and the Moon). Jenny is forced to choose between her relationship with Eric (recurring guest star CONNOR PAOLO) and her new role as Queen Bee. Plus, Rufus gets Lily into the Halloween spirit. Musician ALBERT HAMMOND JR. (The Strokes) performs.
The Grandfather: Part II
Season 1, Episode 51 Unrated
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Olivia (recurring guest star HILARY DUFF) says something she regrets during an appearance on a talk show with host JIMMY FALLON (guest starring as himself) and tries to keep Dan from finding out. With election day around the corner, Nate suspects his grandfather (recurring guest star JAMES NAUGHTON) will stop at nothing to get Tripp (recurring guest star AARON TVEIT) elected to Congress. In the midst of another feud with Serena, Blair befriends a new It girl. In an effort to make Serena jealous, Blair takes her new friend to an election night party at Chuck's hotel.
They Shoot Humphreys, Don't They?
Season 1, Episode 52 Unrated
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Not satisfied with just being Queen of Constance Billard, Jenny sets her sights on becoming the queen of all the Upper East Side by landing the hottest escort for Cotillion. Nate and Chuck plot to help Serena and Blair repair their damaged friendship. Dan is upset when Olivia (recurring guest star HILARY DUFF) contemplates leaving school for a movie project. Plus, all-girl French rock band PLASTISCINES performs.
The Last Days of Disco Stick!
Season 1, Episode 53 Unrated
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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 (in a special guest performance). Dan and Olivia (recurring guest star 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 a difficult situation. As a favor to Chuck, Jenny agrees to hang out with Damian (recurring guest star KEVIN ZEGERS - Transamerica, The Jane Austen Book Club, Dawn of the Dead), 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.
The Treasure of Serena Madre
Season 1, Episode 54 Unrated
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How about an extra helping of drama this holiday season? It just wouldn't be Thanksgiving on the Upper East Side without it. Blair suspects her mom (recurring guest star MARGARET COLIN) 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 (recurring guest star GINA TORRES) and shows up on Dan's doorstep. Meanwhile, Rufus learns that Lily has been lying to him about her mother, Cece (recurring guest star CAROLINE LAGERFELT), and Chuck tells Nate that he has some potentially damaging information about one of their friends. Plus, Jenny learns that Eric (recurring guest star CONNOR PAOLO) was behind her very public embarrassment at Cotillion and can't pass up a chance to get even. And Serena is put in a very awkward position when her mother invites Tripp (recurring guest star AARON TVEIT) and Maureen (recurring guest star HOLLEY FAIN) to join them for Thanksgiving dinner.
The Debarted
Season 1, Episode 55 Unrated
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On the anniversary of the death of Bart Bass, 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. And when Jenny is accused of beating up one of her classmates, Eric (recurring guest star CONNOR PAOLO) is faced with a tough dilemma.
The Hurt Locket
Season 1, Episode 56 Unrated
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Nate and Serena explore the boundaries of their friendship. Blair suspects that Chuck is having problems forgetting about the woman (recurring guest star LAURA HARRING - The Shield, Mulholland Drive, Sunset Beach) he saw at his father's grave. Jenny agrees to help Damien (recurring guest star KEVIN ZEGERS) overcome a challenge he faces. Vanessa and Dan attempt to move past the awkwardness of Dan's confession of love. Rufus returns from a ski trip and tries his best to avoid Lily.
The Lady Vanished
Season 1, Episode 57 Unrated
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Chuck learns more about the woman (recurring guest star LAURA HARRING - The Shield, Mulholland Drive, Sunset Beach) who may or may not be his mother. Dan and Vanessa struggle through the awkwardness of dating other people. Plus, Rufus and Lily grow suspect of Jenny's relationship with Damien (recurring guest star KEVIN ZEGERS).
The Sixteen Year Old Virgin
Season 1, Episode 58 Unrated
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Jenny contemplates taking her relationship with Damian (recurring guest star KEVIN ZEGERS) to the next level, and Nate and Serena clash over how to handle the situation. Meanwhile, a bogus lawsuit threatens to shut down Chuck's hotel, and he suspects his uncle, Jack Bass (recurring guest star DESMOND HARRINGTON), is behind it. Chuck's doubt that his mother (recurring guest star LAURA HARRING) may not be who she claims to be could destroy their newly formed bond. Plus, Dan and Vanessa attempt to define the different "zones" of their relationship, and Lily and Rufus try to trust one another.
The Empire Strikes Jack
Season 1, Episode 59 Unrated
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Chuck, once again, finds himself at odds with his uncle, Jack Bass (recurring guest star DESMOND HARRINGTON). Eleanor (recurring guest star MARGARET COLIN) puts Blair in charge of making sure her latest fashion show is a huge success with an important client. Rufus attempts to get Jenny back on track by volunteering to have her help with Eleanor's fashion show, but the opportunity takes a turn for the worse when Jenny learns that Agnes (recurring guest star WILLA HOLLAND) will be one of the models.
Inglorious Bassterds
Season 1, Episode 60 Unrated
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Chuck and Blair are faced with the most difficult decision they have ever faced as a couple. Serena plans a surprise birthday party for Nate, but Jenny does her best to sabotage Serenas's efforts. Meanwhile, Dan and Vanessa's new relationship hits a bump in the road.
The Unblairable Lightness of Being
Season 1, Episode 61 Unrated
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Chuck offers to throw a wedding for a very pregnant Dorota (recurring guest star ZUZANNA SZADKOWSKI) who insists that she and Vanya (recurring guest star AARON SCHWARTZ) have a traditional wedding before her parents arrive from Poland and find their daughter pregnant and without a husband. Dorota asks Blair and Chuck to be part of the ceremony and walk her down the aisle. Serena tells Nate she is having breakfast with the Humphreys when in reality she is secretly meeting up with Carter Baizen (recurring guest star SEBASTIAN STAN). Plus, Rufus discovers that Lily has been lying to him about her whereabouts.
Dr. Estrangeloved
Season 1, Episode 62 Unrated
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When Lily's ex-husband Dr. William van der Woodsen (recurring guest star WILLIAM "BILLY" BALDWIN – Dirty Sexy Money, Backdraft), shows up unexpectedly in Manhattan, Serena finally gets the reunion with her father she has so desperately wanted — but the circumstances turn out to be far from ideal. Meanwhile, Serena and Nate continue to have relationship issues, and a scheming Jenny is more than happy to be a shoulder for Nate to lean on. Plus, Dan finds out that he didn't get accepted into the Tisch writing program and Vanessa admits she may have been somewhat responsible.
It's A Dad, Dad, Dad, Dad World
Season 1, Episode 63 Unrated
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Will's (recurring guest star WILLIAM "BILLY" BALDWIN) return to the Upper East Side continues to stir up problems for Serena, Lily and Will's long-standing rival, Rufus. The relationship between Serena and Jenny is strained as a result of Jenny's deception. Blair spends time on the Columbia campus and realizes where she truly belongs. And Dan learns that Vanessa has been keeping yet another secret from him.
Ex-Husbands and Wives
Season 1, Episode 64 Unrated
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When things get tense between Rufus and Will (recurring guest star WILLIAM "BILLY" BALDWIN), Serena chooses to stand behind her father, while Rufus is made to feel like an outsider within his own family. Meanwhile, Jenny deliberately shares information with Will that may ultimately destroy Lily and Rufus' marriage. And, after many failed attempts, Chuck makes one last grand gesture to reconcile with Blair, hoping she will finally accept the fact that they are destined to be together.
Last Tango, Then Paris
Season 1, Episode 65 Unrated
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In the third season finale, Blair must decide whether to meet Chuck at the top of the Empire State Building or risk losing their future together. A Gossip Girl gossip bomb involving Dan explodes Serena and Nate's relationship. Dorota (recurring guest star ZUZANNA SZADKOWSKI) and Vanya (recurring guest star AARON SCHWARTZ) welcome their baby. Jenny hits rock bottom. Plus, Georgina (recurring guest star MICHELLE TRACHTENBERG) returns to the Upper East Side … and she has an agenda.
Belles de Jour
Season 1, Episode 66 Unrated
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Season four kicks off in the City of Lights — Paris! Blair has spent a fabulous summer in Paris without realizing Chuck, her former love, has been shot. Yet as much as Blair tries to distract herself from the pain Chuck caused her by sleeping with Jenny Humphrey, his mysterious appearance in Paris with a beautiful new woman will force both of them to face what happened. Serena has been enjoying a Parisian summer of love with boys, Blair and Balenciaga as she tries to avoid the inevitable decision about which of her two longtime beaus, Dan or Nate, she should return to. Meanwhile, back on the Upper East Side of Manhattan, Nate meets an intriguing girl, Juliet, who helps him realize that his summer of sexual conquests was his way of avoiding his unresolved feelings for Serena. Plus, Dan's baby mama drama continues with Georgina and the van der Woodsen apartment is buzzing with activity as a "Fashion's Night Out" event is planned.
Double Identity
Season 1, Episode 67 Unrated
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Living out a real-life fairytale in Paris, Blair is pursued by a handsome young man, Louis (guest star HUGO BECKER), whom Blair suspects is a member of Monaco's royal family. A very concerned Lily asks Serena to help her find Chuck, who hasn't been heard from or seen in months. Meanwhile, Chuck Bass is as we've never seen him before, adjusting to a fresh start in Paris with a mysterious new woman, Eva (recurring guest star CLÉMENCE POÉSY), at his side. And Juliet (recurring guest star KATIE CASSIDY) offers to help Nate win Serena back, suggesting that by reigniting the romance between Dan and Vanessa, it may remove Dan from the Dan-Serena-Nate love triangle.
The Undergraduate
Season 1, Episode 68 Unrated
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It's back to the Upper East Side! On her first day at Columbia, Blair attempts to gain membership into an ultra-exclusive social club, Hamilton House, but she's in for a few big surprises. Serena begins to suspect that her life is being intentionally sabotaged by Juliet (recurring guest star KATIE CASSIDY), and that it may have something to do with Nate. Meanwhile, Rufus is worried about Dan and decides to take matters into his own hands.
Touch of Eva
Season 1, Episode 69 Unrated
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Nate suspects that Juliet (recurring guest star KATIE CASSIDY) is keeping a big secret from him and decides to confront her. Blair schemes to undermine Chuck's newfound happiness. Dan finds himself torn between his feelings for Serena and Vanessa.
Goodbye, Columbia
Season 1, Episode 70 Unrated
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An anonymous Gossip Girl blast starts a very damaging rumor about one of Columbia's new students, Serena. On her path to greatness, Blair decides to take a class with a powerful businesswoman, Martha (guest star MARLYNE BARRETT – Damages, Kings, The Wire), who is a guest lecturer at Columbia, but a mysterious fellow student thwarts her plans to secure the prized position as Martha's assistant.
Easy J
Season 1, Episode 71 Unrated
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Although Blair made it perfectly clear that Little J was no longer welcome in Manhattan after what happened with Chuck, Jenny is tempted by a once-in-a-lifetime opportunity to meet Tim Gunn (guest star TIM GUNN – Project Runway), which could be a game changer for her future. Meanwhile, Serena discovers something about her new boyfriend, Colin (guest star SAM PAGE – Mad Men, Desperate Housewives, Shark), that may put an end to their relationship just as it was getting good.
War at the Roses
Season 1, Episode 72 Unrated
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Blair is caught off-guard — and not in a good way — by a surprise guest at her birthday party. Having had enough of Chuck and Blair's games, Serena and Nate decide to plan an intervention. Musical guest ROBYN performs.
Juliet Doesn't Live Here Anymore
Season 1, Episode 73 Unrated
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Chuck and Blair decide it's in both of their best interests to put the past behind them and end their vindictive games. Nate confronts Juliet (recurring guest star KATIE CASSIDY) after discovering a secret she has been keeping from everyone. Dan and Nate realize they both still have feelings for Serena.
The Witches of Bushwick
Season 1, Episode 74 Unrated
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Chuck hosts a "Saints and Sinners" masquerade party at the Empire Hotel. At the party, Dan and Nate don't know what to make of Serena's strange behavior and mixed messages. Blair sets her sights on becoming the new face of Anne Archibald's (recurring guest star FRANCIE SWIFT – The Good Wife) foundation for girls, but Anne is concerned that Blair's friendship with Chuck Bass may be problematic. Recurring guest star KATIE CASSIDY appears as Juliet.
Gaslit
Season 1, Episode 75 Unrated
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Chuck, Serena, Blair, Dan, Jenny and Eric (recurring guest star CONNOR PAOLO) find themselves faced with a crisis when a member of one of their families is hospitalized. Meanwhile, Nate attempts to help his parents, the Captain (recurring guest star SAM ROBARDS) and Anne (recurring guest star FRANCIE SWIFT), put their complicated past behind them and reconcile. Recurring guest star KATIE CASSIDY appears as Juliet.
The Townie
Season 1, Episode 76 Unrated
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Blair and Dan join forces to track down Juliet (recurring guest star KATIE CASSIDY), who is missing in action. Meanwhile, Chuck begins to suspect Lily isn't telling him the full truth. Recurring guest star KEVIN ZEGERS (Transamerica, Dawn of the Dead) appears as Damien.
The Kids Are Not All Right
Season 1, Episode 77 Unrated
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Russell Thorpe (MICHAEL BOATMAN), a former associate of Chuck's father, and his daughter, Raina (TIKA SUMPTER), return to Manhattan with some unfinished business.
Damien Darko
Season 1, Episode 78 Unrated
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Blair is ecstatic to land an internship at W magazine, but the thrill quickly fades when she finds out that Dan has secured one of the coveted positions as well. Chuck may have finally met his match now that Russell Thorpe (recurring guest star MICHAEL BOATMAN) and his daughter, Raina (recurring guest star TIKA SUMPTER), are back on the Upper East Side. Meanwhile, Nate receives alarming news about his father's (recurring guest star SAM ROBARDS) business prospects.
Panic Roommate
Season 1, Episode 79 Unrated
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Blair enlists Nate's help to win over her high-strung boss, Epperly (recurring guest star CAITLIN FITZGERALD – It's Complicated), at W magazine. Meanwhile, Damien (recurring guest star KEVIN ZEGERS) stirs up more drama on the Upper East Side and Chuck finds himself torn between business and pleasure. Plus, musical sensation FLORENCE AND THE MACHINE performs an acoustic version of "Cosmic Love."
It-Girl Happened One Night
Season 1, Episode 80 Unrated
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With Russell Thorpe (recurring guest star MICHAEL BOATMAN) poised for a takeover attempt of Bass Industries, Chuck makes one last-ditch effort to save his family's company. Meanwhile, Blair is given a challenging assignment at W magazine with the promise of a possible promotion, and Serena struggles with her feelings for Ben (recurring guest star DAVID CALL – Rescue Me, Fringe).
While You Weren't Sleeping
Season 1, Episode 81 Unrated
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It wouldn't be a proper Upper East Side party without some major Gossip Girl drama, and for Eric's (recurring guest star CONNOR PAOLO) 18th birthday celebration there is plenty to go around. Blair decides to speed up the time table on her career path to becoming a powerful woman, but ultimately stretches herself too thin. Serena is forced to choose between her family and Ben (recurring guest star DAVID CALL). And Chuck and Lily's relationship remains icy in the aftermath of Lily's betrayal.
Empire of the Son
Season 1, Episode 82 Unrated
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Ben's (DAVID CALL) mother (MARSHA DIETLEIN BENNETT) comes to town, forcing issues to the surface between Ben and Serena. BILLY BALDWIN appears as William van der Woodsen.
The Kids Stay in the Picture
Season 1, Episode 83 Unrated
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Lily’s family offers support and takes part in a Taschen photo shoot on “modern royalty.” BILLY BALDWIN, CAROLINE LAGERFELT, SHEILA KELLEY, KAYLEE DeFER guest star.
Petty in Pink
Season 1, Episode 84 Unrated
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Serena enlists Charlie (recurring guest star KAYLEE DeFER) to go undercover, Gossip Girl–style, to determine why Dan and Blair are spending so much time together and what role an unexpected visitor is playing in their lives. Meanwhile, with Nate’s help, Raina (recurring guest star TIKA SUMPTER) decides to go on a search for her long-lost mother, and Chuck’s hopes about his legacy are dashed with the reveal of devastating information from the past.
The Princesses and the Frog
Season 1, Episode 85 Unrated
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Blair’s dreams appear to be coming true, but Serena threatens to jeopardize it all by dredging up Blair’s past. Charlie (recurring guest star KAYLEE DeFER) befriends Vanessa, who may or may not have a hidden agenda. Nate is torn between his relationship with Raina (recurring guest star TIKA SUMPTER) and a truth he must keep hidden out of loyalty to Chuck.
Shattered Bass
Season 1, Episode 86 Unrated
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Charlie (recurring guest star KAYLEE DeFER) is finally starting to feel less like a fish-out-of-water with Serena and her friends, but complications present themselves when Charlie is invited to attend the Constance Billard alumni fundraiser. On the road to “happily ever after,” Blair finds herself torn between the men in her life, and Jack Bass’ (recurring guest star DESMOND HARRINGTON) return to the Upper East Side sets off a chain of events that could end up destroying Chuck and those closest to him.
The Wrong Goodbye
Season 1, Episode 87 Unrated
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The explosive season four finale features the return of Georgina Sparks (recurring guest star MICHELLE TRACHTENBERG) and Constance Billard mean girls Kati and Is (recurring guest stars NAN ZHANG and NICOLE FISCELLA), a cameo by Gossip Girl author CECILY VON ZIEGESAR, a musical performance by AIRBORNE TOXIC EVENT and — oh, yeah — a few very juicy cliffhangers.
Yes, Then Zero
Season 1, Episode 88 Unrated
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In the fifth season premiere, Serena loves her new job in Hollywood, but makes a costly misstep when she tries to impress her boss (recurring guest star MICHAEL MICHELE – ER, Homicide: Life on the Street, Ali). Chuck and Nate arrive in Los Angeles as the last stop of their trip around the globe, joining Serena at a glamorous Hollywood Hills party, where Nate meets a sexy older woman (recurring guest star ELIZABETH HURLEY). Meanwhile, Blair and Louis (recurring guest star HUGO BECKER) return from Monaco and begin planning their royal wedding, but when Louis refuses to stand up to his family and support Blair’s choices, his weakness threatens their relationship. Plus, a magazine is planning to run an excerpt of Dan’s book until an unlikely ally steps in to help him kill the story.
Beauty and the Feast
Season 1, Episode 89 Unrated
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Nate reconnects unexpectedly with Diana (ELIZABETH HURLEY), who offers him an exciting opportunity. Blair’s future sister-in-law, Beatrice (ROXANE MESQUIDA), arrives from Monaco.
The Jewel of Denial
Season 1, Episode 90 Unrated
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At Diana’s (recurring guest star ELIZABETH HURLEY) request, Nate must decide whether to cross moral lines. Dan figures out who is publishing his book and seeks help to stop it, but he still ends up in the spotlight. Chuck helps Dan come to terms with his fate, just as Dan continues to try to help Chuck break through his emotional block. Plus, Serena and Charlie return to the Upper East Side from California, and a Jenny Packham fashion show is featured.
Memoirs of an Invisible Dan
Season 1, Episode 91 Unrated
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After much deliberation, Dan decides to gather Serena, Blair, Nate, Chuck, Rufus and Lily to reveal the truth about his book in the hope that they will support him at his book party. Meanwhile, Blair and Louis (recurring guest star HUGO BECKER) enter crisis status after Louis reads Dan’s book. Diana (recurring guest star ELIZABETH HURLEY) learns incriminating information about one of Nate’s friends and uses it to her advantage.
The Fasting and the Furious
Season 1, Episode 92 Unrated
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In the midst of celebrating Yom Kippur with family and friends, Blair and Louis (recurring guest star HUGO BECKER) find themselves in a power struggle with Louis’ family. Serena’s boss (recurring guest star MICHAEL MICHELE) puts Serena in the awkward position of choosing between her new job and her relationship with Dan. Meanwhile, Diana (recurring guest star ELIZABETH HURLEY) prepares to debut the New York Spectator, but an unfortunate last-minute surprise delays the launch and Diana expects Nate to do whatever it takes to save the day.
I Am Number Nine
Season 1, Episode 93 Unrated
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Blair makes her former minions and Charlie compete for the coveted bridesmaid spots in her upcoming royal wedding. Nate uses Charlie to make Diana (ELIZABETH HURLEY) jealous.
The Big Sleep No More
Season 1, Episode 94 Unrated
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Several of our favorite Upper East Siders attend a performance of Punchdrunk’s provocative theater experience “Sleep No More,” which means masks, anonymity and some surprising romantic twists by the end of the evening. Meanwhile, Diana (recurring guest star ELIZABETH HURLEY) sets her sights on Serena in her quest to ruin Gossip Girl. Plus, Dan is out on his book tour, but things aren’t exactly as they appear to his friends and family.
All the Pretty Sources
Season 1, Episode 95 Unrated
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Serena plans a dream bridal shower for Blair, but Chuck and Dan don’t make the guest list. Nate and Serena make a discovery in Diana’s (ELIZABETH HURLEY) war against Gossip Girl.
Rhodes to Perdition
Season 1, Episode 96 Unrated
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Lily, Charlie and Serena eagerly anticipate the Studio 54 party being thrown in CeCe’s (recurring guest star CAROLINE LAGERFELT) honor. Nate takes on a new role at the Spectator, but his first big story turns out to be about someone he knows all too well. Blair turns to an unlikely person for help.
Riding in Town Cars with Boys
Season 1, Episode 97 Unrated
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Lily throws Charlie a party to officially introduce her to New York society. Meanwhile, Charlie’s ex-boyfriend, Max (recurring guest star BRIAN J. SMITH – SGU Stargate Universe), throws a wrench into Charlie’s future as an Upper East Side princess. Dan decides it may be time to tell Blair the truth about his feelings for her.
The End of the Affair?
Season 1, Episode 98 Unrated
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Through a series of emotional flashbacks, Blair reveals to Serena what really happened in the aftermath of her tragic car accident with Chuck. VERA WANG appears as herself.
Father and The Bride
Season 1, Episode 99 Unrated
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Blair prepares to celebrate her upcoming royal wedding with a bachelorette party, but others scheme behind her back to make this a night to remember. After discovering the truth behind Chuck and Blair’s car accident, Nate joins forces with a surprising ally to gather the evidence. Serena and Dan pretend to be dating again to protect someone close to them.
G.G
Season 1, Episode 100 Unrated
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The much-anticipated 100th episode will open with a musical dream sequence featuring Serena, Blair and all the men in their lives. Also, while Chuck wrestles with the reality that Blair is about to walk down the aisle with Prince Louis (recurring guest star HUGO BECKER), the return of Georgina Sparks (recurring guest star MICHELLE TRACHTENBERG) might make the royal affair a royal disaster.
The Back Up Dan
Season 1, Episode 101 Unrated
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Blair must make a difficult decision about her future, the consequences of which could hurt those she loves most. Serena takes the blame for an incident with Gossip Girl in order to protect someone she loves. Georgina (recurring guest star MICHELLE TRACHTENBERG) smells the scent of scandal and decides to follow its trail.
Crazy, Cupid, Love
Season 1, Episode 102 Unrated
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It’s Valentine’s Day on the Upper East Side and Blair can’t resist playing cupid for someone she loves. Georgina (recurring guest star MICHELLE TRACHTENBERG) is intent on stirring up more drama, so she decides to crash Nate’s Valentine’s Day party. Meanwhile, Serena is shocked by something she witnesses at the party. Musical group ST. VINCENT performs.
Cross Rhodes
Season 1, Episode 103 Unrated
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Dan feels honored when he learns that comedy troupe Upright Citizen’s Brigade is performing excerpts from his book, Inside. Blair tries to prove Serena’s suspicions wrong in order to save their friendship. And, on her way out of town, Ivy ends up on a collision course with the van der Woodsens.
The Princess Dowry
Season 1, Episode 104 Unrated
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Blair thinks a potential loophole may have been found in her pre-nuptial agreement. Chuck and Georgina (recurring guest star MICHELLE TRACHTENBERG) partner up in a scheme, but it has an unpredictable outcome. Meanwhile, a family crisis brings William van der Woodsen (recurring guest star BILLY BALDWIN) back to the Upper East Side.
Con Heir
Season 1, Episode 105 Unrated
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Chuck invites Jack (recurring guest star DESMOND HARRINGTON) to town to thank him for saving his life, but finds the trip doesn’t go exactly as planned. Blair and Dan attempt to consummate their new relationship — but unexpected roadblocks get in their way. Meanwhile, Ivy finds an unlikely ally in William (recurring guest star BILLY BALDWIN) in her quest to be accepted on the Upper East Side, and Nate is hopeful a new investor will save his newspaper.
It Girl, Interrupted
Season 1, Episode 106 Unrated
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Serena decides she is ready to relinquish the spotlight and sets out to make a reluctant Lola (recurring guest star ELLA RAE PECK – The Good Wife) the next It Girl of the Upper East Side, starting with modeling at a Kiki de Montparnasse party and lingerie show. Meanwhile, Chuck reaches out to Blair for advice about his past, and Diana Payne’s (recurring guest star ELIZABETH HURLEY) return to The Spectator starts a power struggle with Nate.
Salon of the Dead
Season 1, Episode 107 Unrated
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To celebrate their official coming out as a couple, Blair and Dan host a glamorous British-themed Salon, including guests JULIAN TEPPER and JENNA GRIBBON (founders of The Oracle Club). Lola (recurring guest star ELLA RAE PECK) lands the audition of a lifetime, but Gossip Girl may have other plans for the Upper East Side’s latest It Girl. Meanwhile, Lily and Rufus disagree over the best way to handle the Ivy situation, and Serena and Diana (recurring guest star ELIZABETH HURLEY) face off over secrets they both would prefer remain secrets.
Despicable B
Season 1, Episode 108 Unrated
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Blair feels like her Upper East Side status might be slipping away and devises a plan to assure that doesn’t happen. Meanwhile, Lily throws a family gathering — including William (recurring guest star BILLY BALDWIN), Carol (recurring guest star SHEILA KELLY) and Lola (recurring guest star ELLA RAE PECK) — in an attempt to prove the van der Woodsen family is as united as ever. Finally, Nate digs into Diana’s (recurring guest star ELIZABETH HURLEY) past and is surprised by what he discovers. New York Social Diary’s DAVID PATRICK COLUMBIA appears in the episode as himself.
Raiders of the Lost Art
Season 1, Episode 109 Unrated
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Chuck, Nate, Blair, Serena and Lola (recurring guest star ELLA RAE PECK) team up to uncover what they think is an explosive secret between Diana (recurring guest star ELIZABETH HURLEY) and Jack (recurring guest star DESMOND HARRINGTON). Meanwhile, Dan is offered a prestigious fellowship in Rome for the summer.
The Fugitives
Season 1, Episode 110 Unrated
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Blair enlists Serena to be her stand-in at an important meeting when Blair finds herself needing to be in two places at the same time. Meanwhile, Ivy and Lola (recurring guest star ELLA RAE PECK) team up to help Chuck with a personal vendetta, and Nate makes a decision about the future with Diana Payne (recurring guest star ELIZABETH HURLEY).
The Return of the Ring
Season 1, Episode 111 Unrated
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In the fifth season finale, when Gossip Girl goes after Blair as never before, Serena admits she may have unintentionally played an important role in Blair’s latest nightmare. Meanwhile, Nate invites Lola (recurring guest star ELLA RAE PECK) to move in with him, and Lily must make a big decision about the future of her marriage. Finally, by episode’s end, Blair will make a choice between the two men in her life … will it be Chuck or will it be Dan?
Gone Maybe Gone
Season 1, Episode 112 Unrated
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In the sixth season premiere, after a brief encounter abroad, Chuck and Blair make a promise to each other about their relationship … which leaves them once again apart. Dan, with some help from an unlikely ally, Georgina Sparks (recurring guest star MICHELLE TRACHTENBERG), is writing a scathing tell-all book that can only mean trouble. Meanwhile, as the sole head of The Spectator, Nate is making his own decisions and is ready to go up against Gossip Girl. As word spreads that Serena is missing, the gang bands together to find her and are shocked by what they find. Recurring guest stars also include BARRY WATSON (7th Heaven, Samantha Who?) as Steven, ANDREA GABRIEL (Lost) as Amira, ROBERT JOHN BURKE (Person of Interest, Rescue Me) as Bart Bass and SOFIA BLACK-D’ELIA (Skins) as Sage.
High Infidelity
Season 1, Episode 113 Unrated
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Trying to prove herself in adult society, Serena hosts the Central Park Conservancy’s big gala, of which she is now the newest Board Member, and she and Nate both learn something shocking about their significant others. Blair prepares to debut her new fashion line, but a rival from her past holds the key to her future. With the help of Georgina (recurring guest star MICHELLE TRACHTENBERG), Dan lands some meetings with publishers, but he must decide if he is willing to sacrifice his integrity in order to get his work published. Meanwhile, Chuck tries to persuade Amira (recurring guest star ANDREA GABRIEL) to help him look into his father’s past, even if it means jeopardizing Lily and Bart’s (recurring guest star ROBERT JOHN BURKE) relationship. Recurring guest stars BARRY WATSON and SOFIA BLACK-D’ELIA also appear.
Dirty Rotten Scandals
Season 1, Episode 114 Unrated
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Feeling the pressure to make her first Waldorf Designs fashion show a success, Blair must rely on help from an unlikely source, but some unexpected scheming causes a scandal on the runway. Serena discovers that befriending Steven’s (recurring guest star BARRY WATSON) daughter, Sage (recurring guest star SOFIA BLACK-D’ELIA), is trickier than she thought, especially when she is forced to put her issues with Blair aside to make Sage happy. Nate publishes Dan’s first serialized article, causing a stir and producing a serious threat. Meanwhile, Chuck begins to look into the clue that Amira (recurring guest star ANDREA GABRIEL) left behind, which may help uncover what Bart (recurring guest star ROBERT JOHN BURKE) is hiding. Plus, style icon ALEXA CHUNG makes an appearance.
Portrait Of A Lady Alexander
Season 1, Episode 115 Unrated
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Chuck’s continued investigation into his father’s dealings leads him to an unlikely event with Manhattan’s elite, where he hopes to find the one person who can tell him the truth about Bart (recurring guest star ROBERT JOHN BURKE). Serena and Steven (recurring guest star BARRY WATSON) decide to reveal their romantic histories so they aren’t surprised by anything, but neither is prepared for what is uncovered. With The Spectator in jeopardy after Dan decided to publish elsewhere, Nate must make a difficult decision to keep it in business. Meanwhile, Georgina (recurring guest star MICHELLE TRACHTENBERG) pushes Dan to choose a worthy person to date in an effort to boost his image, but he finds himself drawn in a different direction.
Monstrous Ball
Season 1, Episode 116 Unrated
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After Blair’s mother, Eleanor (recurring guest star MARGARET COLIN), gives Blair an ultimatum, Blair is even more determined to remedy Waldorf Designs’ problems by making a splash with a dress at the upcoming Cotillion — but a shocking revelation at the ball affects everyone. Serena becomes worried about Steven’s (recurring guest star BARRY WATSON) attitude toward her, but after some investigating she discovers the surprising reason why. Chuck finds an unlikely ally as he tries to drive a wedge between Bart (recurring guest star ROBERT JOHN BURKE) and Lily’s relationship to help expose his father’s secret. Meanwhile, Dan publishes another article, but the effect is just the opposite of what he was hoping for.
Where The Vile Things Are
Season 1, Episode 117 Unrated
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Blair gets ready for her mother’s (recurring guest star MARGARET COLIN) imminent arrival, but is unprepared for the set of demands her mother puts upon her. Serena volunteers to help Dan find a new place to live, but their time together brings up unexpected emotions. With Ivy’s help, Chuck discovers there is evidence incriminating his father in illegal activities and enlists the help of Nate to retrieve it. Meanwhile, Rufus and Ivy are excited about their art gallery opening until they find an empty RSVP list and must scramble to find another way to make the event a success.
Save The Last Chance
Season 1, Episode 118 Unrated
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Serena and Dan realize that they need to make amends with the people they have wronged. Blair has one last chance to prove to her mother her worth as a fashion designer and, with Serena’s help, comes up with a plan to make her line the “it” look for Sage (recurring guest star SOFIA BLACK-D’ELIA) and her friends. Meanwhile, Chuck is close to getting the evidence he needs against his father, until one of his closest allies reveals his plan to Bart (recurring guest star ROBERT JOHN BURKE). Recurring guest stars MICHELLE TRACHTENBERG and WILLIAM BALDWIN appear as Georgina Sparks and William van der Woodsen, respectively.
It's Really Complicated
Season 1, Episode 119 Unrated
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What’s Thanksgiving without a side of drama? Serena and Dan decide to throw their first Thanksgiving together, inviting only their closest friends, but everyone seems to have their own agenda for attending. Feeling defeated by his father (recurring guest star ROBERT JOHN BURKE), Chuck begins a downward spiral, leaving Blair to find a solution to his problems. Meanwhile, Dan has written his latest exposé, but he must make a tough decision whether to publish it, knowing it could destroy a close friendship. Recurring guest stars SOFIA BLACK-D’ELIA and BARRY WATSON appear as Sage and Steven, respectively.
The Revengers
Season 1, Episode 120 Unrated
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After a run-in with an increasingly paranoid Bart Bass (recurring guest star ROBERT JOHN BURKE), Blair grows alarmingly concerned for Chuck’s safety. However, feeling confident that his father would never physically hurt him, Chuck makes a deal that could change his life. Wanting to make things better for Chuck, Blair devises a plan with the help of Serena, Georgina (recurring guest star MICHELLE TRACHTENBERG) and Sage (recurring guest star SOFIA BLACK-D’ELIA) to try and get what they need out of Bart. Meanwhile, Nate’s financial dilemma finally lands him in a place that he never thought he would be.
New York, I Love You XOXOXO
Season 1, Episode 121 Unrated
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Series finale! In a fashionable farewell to remember, our favorite Upper East Siders join forces for one last soiree, and the shocking identity of Gossip Girl is finally revealed.
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