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Jenny’s kinda-not-sweet sixteen!

Serena throws Jenny an small birthday party for her sweet sixteenth, but things get out of control when Poppy Lifton turns the birthday into a huge social event. Vanessa in a moment of desesperation agrees to help Chuck with a scheme having to do with Blair and Nate. Rufus tries to figure out how to cover Dan’s Yale tuition, when he learns that Dan will not receive financial aid.

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Devastated by her current situation (not being accepted by Yale), Blair begins to explore her dark side with the help of Carter Baizen. This causes her friends Serena and Chuck to become worried about her well-being. Meanwhile, Vanessa convinces Nate to reconcile with his maternal grandfather, a very rich and powerful man who abandoned Nate and his mother when they needed help the most. Wanting to have nothing to hide from each other, Lily and Rufus agree to share lists of their past lovers, but this turns out not to be such a great idea.

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• Gossip Girl Season 2 Episode 19 - The Grandfather
• Season 2 Episode 19: The Grandfather

Serena develops a crush on the director of the school play; Blair gets devastating news about her future; Dan and Rachel have a hard time staying away from each other.

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

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Who will get in the Ivy League institution of their choice? The students find out who is worthy of an early admission to Yale. Serena connects with a new Shakespeare teacher, who has no clue about what is going to happen when she gives Blair the first B grade in her life. Chuck pairs up with an unlikely ally in his battle over Bass Industries. Nate and Vanessa have a romantic night at the opera.

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A sudden tragedy strikes the lives of every teen and parent on the Upper East Side.

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Chuck and Blair make a bet to choose the perfect date for each other for the annual Snowflake Ball. Lexi has her sights set on Dan leaving Serena confused with her feelings. Nate and Vanessa are forced to be together leaving their emotions and friendship in danger of being burnt.

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

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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 naívely agrees to babysit the 15-year-old daughter of a prominent Yale donor. Unfortunately, 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.

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Jenny has a new young model friend, Agnes, who encourages Jenny to explore her wild side and to confront Eleanor Waldorf, who is exploiting Jenny by stealing her designs with false promises to help launch her design career. Meanwhile, Serena and Dan attend Rufus’ art opening as friends, but when Serena meets a cute artist, the evening takes an awkward turn. Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined.

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