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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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In the reading of Bart’s will, Chuck, Bart’s brother, Jack and Lily learn that Chuck is now the CEO of Bass Industries. Chuck agrees that Jack became his guardian.

Rufus and Lily’s relationship is strained as Rufus searches for details about the child he never knew he had. Noticing the strange way his father has been acting lately, Dan does some investigating and uncovers Rufus and Lily’s secret, and he has to decide now what to do and who to tell the shocking revelation.

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Because Chuck is MIA since his father’s funeral, his Uncle Jack arrives on the Upper East Side to find and help him. Trying to forget her last conversation with Chuck, Blair focuses 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.

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

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