On 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.
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Blair 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.
Trying 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.
Jenny 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.
Olivia, 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.
Looking 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.
Vanessa 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.
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.
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.
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.