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5/17/10Blair has to decide between meeting Chuck at the Empire State Building or risking their future together. A gossip about Dan causes problems for Serena and Nate. Dorota and Vanya welcome their baby. Jenny hits rock bottom. Meanwhile, Georgina Sparks returns to the Upper East Side with an agenda.
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5/10/10Things start to get tense between Rufus and Will, and Serena chooses to stand by her father, while Rufus starts to feel like an outsider in his own home. Meanwhile, Jenny deliberatly tells Will something that can destroy Lily and Rufus' marriage. After many attempts, Chuck makes the ultimate grand gesture to get Blair back, hoping that she realizes that they are destined to be together.moreless
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5/3/10Serena's father, Dr. William van der Woodsen, returns to the Upper East Side and ensues conflict with Serena, Lily, and Rufus. Because of Jenny's recent actions, Serena's and Jenny's step-sister bond enxounters an obstacle. Blair finds the college where she belongs when she visits the Colombia campus. Dan discoves another secret that Vanessa has been hiding from him.moreless
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4/26/10Lily, finally, reveals to Rufus where she has been and why she has been lying to him. Chuck, wanting his best friend back, plans with Jenny to break Serena and Nate up. Meanwhile, Serena's father, Dr. William van der Woodsen, returns.
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4/12/10Chuck offers to throw Dorota's wedding before Dorota's parent's arrive from Poland and see her pregnant and without a husband. Dorota asks Blair and Chuck to be part of the ceremony and walk her down the aisle. Meanwhile, Serena lies to Nate telling him she's having breakfast with the Humphreys when in reality she goes to meet with Carter Baizen. Rufus discovers that Lily has been lying to him about where she is.moreless
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4/5/10Chuck and Blair's relationship is faced with the most difficult decision they have ever faced as a couple. Serena plans a surprise birthday party for Nate, but Jenny tries to sabotage her. Meanwhile, Dan and Vanessa's relationship hits a bump in the road.
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3/29/10Jack Bass is back in NY and Chuck finds himself at odds with his uncle. Eleanor puts Blair in charge of making sure her fashion show is a huge success with an important client. Rufus tries to get Jenny to be more good by volunteering to help in Eleanor's fashion show, but it takes a turn for the worse when Jenny finds out that Agnes is one of the models.moreless
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3/22/10Despite being grounded, Jenny continues to see Damien who pressures her to sleep with him. Lily tells Rufus the big secret she has been keeping from him even though she knows it's very risky. Meanwhile, Dan and Vanessa explore the new stage of their friendship, while Chuck is forced to make a very difficult desicion about his hotel.moreless
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3/15/10Rufus and Lily suspect something bad about Jenny's and Damien's relationship. Chuck learns more about the woman at the cemetery who may or may not be his mother. Meanwhile, Dan and Vanessa struggle with the awkwardness of dating other people.
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3/8/10
Nate and Serena explore their friendship. Blair thinks Chuck is having problems forgetting the woman he saw at his father's grave. Jenny go with Damien to a State Dinner but she wasn't aware that it was also to help him with a drug exchange. Vanessa and Dan try to move past Dan's confession. Rufus returns from a ski trip and tries to avoid Lily.
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12/7/09On the anniversary of Bart Bass death, Chuck has to deal with some issues from the past and a car accident disturbs the Upper East Side. Meanwhile, Dan and Vanessa tried to stay in their complicated friendship no matter what. Jenny is accused of beating a classmate, and Eric has to decide which story to beleive.moreless
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11/30/09Blair bid to find out what her Mother is hiding backfires. Vanessa gets into a fight with her mom and ends up at the Humphreys. Rufus is hurt when he discovers Lily has been lying to him. Chuck divulges some news that could ruin a friend to Nate. Jenny finds tries to get even with Eric after learning the truth.moreless
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11/16/09Trying to impress NYU theater kids, Blair uses her contacts to get a private concert with today's hottest performer, Lady Gaga. Dan and Olivia sign up to write and star in an NYU play, based on an idea by Blair and directed by Vanessa. Meanwhile, Serena turns to Nate for help in a dificult situation, now that Blair is not there. As a favor to Chuck, Jenny agrees to hang out with Damien, an ambassador's son staying in Chuck's hotel, and the experience turned out to be more intriguing than what she thought.moreless
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11/9/09Jenny wants to be the Queen Bee of not only Constance but of all the Upper East Side, as she lands the hottest escort for the Cotillion. Meanwhile Dan and Vanessa try to convince Olivia to stay in NY by showing her the "true college experience". Leighton Meester's new single "Somebody to Love" is featured in the episode, along with performance from Plastiscines.moreless
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11/2/09Olivia, as a guest on Jimmy Fallon's talk show, says something she regrets and tries to hide it from Dan. With elections coming up, Nate suspects his grandfather will do everything he has to get Trip into congress. After another fight with Serena, Blair gets a new friend and takes her to an election night party at Chuck's hotel, just to make Serena jealous.moreless
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10/26/09Looking for publicity for his new hotel, Chuck moves his club's opening and convinces Serena to assist him in getting the word out. Feeling left out, Blair tries to win Chuck's approval by secretly helping him with a problem concerning the opening night. Meanwhile, Dan get's nervous after watching one of Olivia's infamous sex scenes with her co-star and real-life boyfriend during that time, Patrick Robinson. Jenny is forced to choose between Eric and her new role as Queen Bee, which as a result causes major conflict between the two characters.moreless
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10/19/09Vanessa desperately trying to have her mom's approval, teams up with Blair to do the honor of delivering the freshman toast at NYU, but what will be the price she has to pay? Dan takes Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple. Meanwhile, Serena and Nate team up to help Carter Baizen.moreless
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10/12/09Lily 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.moreless
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10/5/09It'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.moreless
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9/28/09It'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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9/21/09Blair 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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9/14/09
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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