Olivia (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.
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Episode
Original Air Date
Synopsis
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1. Reversals of Fortune
September 14, 2009
Blair and Chuck adjust to their new status as a couple and Serena returns from Europe with many secrets to hide and a complicated relationship with Carter Baizen (SEBASTIAN STAN).
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$1.99
2. The Freshman
September 21, 2009
Blair begins NYU, determined to keep her Queen Bee status, but Georgina (MICHELLE TRACHTENBERG) has other ideas. And Serena recruits Carter (SEBASTIAN STAN) to get even with Chuck.
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$1.99
3. The Lost Boy
September 28, 2009
It's Blair versus Chuck as they both set their sights on a particular item up for bid at Sotheby's. Plus, Georgina MICHELLE TRACHTENBERG) takes an interest in Dan.
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$1.99
4. Dan de Fleurette
October 5, 2009
It's Jenny's first day as Queen Bee. Plus, a famous actress, Olivia Burke (HILARY DUFF - A Cinderella Story), is assigned as Vanessa's roommate. TYRA BANKS also guest stars.
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$1.99
5. Rufus Getting Married
October 12, 2009
Will Lily and Rufus go through with their planned nuptials? Plus, Dan and Vanessa are pulled into one of Georgina's (MICHELLE TRACHTENBERG) schemes and SONIC YOUTH performs.
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$1.99
6. Enough About Eve
October 19, 2009
Dan invites Olivia (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 (SEBASTIAN STAN).
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$1.99
7. How to Succeed in Bassness
October 26, 2009
Serena helps Chuck open his club, but Blair feels left out. Dan is unnerved watching one of Olivia's (HILARY DUFF) sex scenes with a former co-star. ALBERT HAMMOND JR. performs.
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8. The Grandfather: Part II
November 2, 2009
Olivia (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.
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9. They Shoot Humphreys, Don't They?
November 9, 2009
Jenny sets her sights on landing the hottest escort for Cotillion. Dan is upset when Olivia (HILARY DUFF) contemplates leaving school. All-girl French band PLASTISCINES performs.
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10. The Last Days of Disco Stick!
November 16, 2009
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. LADY GAGA performs.
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11. The Treasure of Serena Madre
November 30, 2009
How about an extra serving of holiday drama? Serena is put in an awkward position when Lily invites Tripp (AARON TVEIT) and Maureen (HOLLEY FAIN) to join them for dinner.
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12. The Debarted
December 7, 2009
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.
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$1.99
13. The Hurt Locket
March 8, 2010
Chuck tracks the woman (LAURA HARRING - The Shield, Mulholland Drive) he saw at his father's grave. Jenny agrees to help Damien (KEVIN ZEGERS). Nate and Serena get friendly.
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$1.99
14. The Lady Vanished
March 15, 2010
Rufus and Lily are suspicious of Jenny's relationship with Damien (KEVIN ZEGERS). Chuck learns more about the mysterious woman (LAURA HARRING - The Shield, Mulholland Drive).
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15. The Sixteen Year Old Virgin
March 22, 2010
Jenny contemplates her relationship with Damian (KEVIN ZEGERS). Dan and Vanessa try to define the different "zones" of their relationship. DESMOND HARRINGTON appears as Jack Bass.
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16. The Empire Strikes Jack
March 29, 2010
Rufus volunteers Jenny to help with Eleanor's (MARGARET COLIN) fashion show, but things take a bad turn when Jenny learns Agnes (WILLA HOLLAND) is one of the models.
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17. Inglorious Bassterds
April 5, 2010
Chuck and Blair are faced with a difficult decision as a couple. Serena plans a surprise birthday party for Nate, but Jenny does her best to sabotage Serenas's efforts.
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18. The Unblairable Lightness of Being
April 12, 2010
Chuck offers to throw a wedding for a very pregnant Dorota (ZUZANNA SZADKOWSKI). Serena doesn't tell Nate she is secretly meeting up with Carter Baizen (SEBASTIAN STAN).
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19. Dr. Estrangeloved
April 26, 2010
When Lily's ex-husband Dr. William van der Woodsen (WILLIAM BALDWIN), shows up unexpectedly, Serena gets the reunion with her father she has so desperately wanted -- or does she?
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20. It's A Dad, Dad, Dad, Dad World
May 3, 2010
Will's (WILLIAM BALDWIN) return to the Upper East Side continues to stir up problems for Serena, Lily and Will's long-standing rival, Rufus. Dan learns Vanessa has another secret.
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21. Ex-Husbands and Wives
May 10, 2010
When things get tense between Rufus and Will (WILLIAM "BILLY" BALDWIN), Serena chooses to stand behind her father, leaving Rufus to feel like an outsider within his own family.
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22. Last Tango, Then Paris
May 17, 2010
Season finale: Blair decides if she'll meet Chuck at the top of the Empire State Building. A Gossip Girl bomb involving Dan explodes. Georgina (MICHELLE TRACHTENBERG) returns.
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Synopsis: Olivia (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.
Synopsis: The O.C. creator Josh Schwartz takes on Manhattan's Upper East Side in this drama where gossip rules and affluent prep-school students find themselves with the money, access and appetite to explore all the temptations New York City has to offer. Based on the best-selling series of young-adult novels by Cecily von Ziegesar.
Season year: 2010
Network: Warner Bros.
ASIN: B002NLY474
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