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

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

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It’s a face-off between Chuck and Blair when they both want to bid on the same item at Sotheby’s. Meanwhile, Serena suspects that Carter may have return to his old habits, while Georgina takes an interest in Dan, and Vanessa suspect something is not right with Scott.

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

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As the summer ends, Blair and Chuck are madly in love and adjusting to their new “in a relationship” status, breaking all traditional rules of dating as would be expected. Serena returns from her European adventure with many secrets to hide and a complicated relationship with Carter Baizen. Nate returns from his travels with a mysterious brunette, Bree Buckley. Rufus, Dan and Jenny spent the summer in the Hamptons, adjusting to the Van Der Woodsen’s glamorous lifestyle much faster than any of them expected.

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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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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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