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High school is officially over for Blair, Serena, Nate, Chuck, Dan, and Vanessa as they leave their carefree days behind and start the new chapter in their life: Adulthood. Still at Constance for their junior year, Jenny and Eric's friendship is tested as Jenny starts her duties as the new Queen of Constance. Chuck purchases The Empire Hotel.
Vanessa attempts to make Nate jealous by kissing Chuck at Jenny's party, but when Nate and Blair appear unfazed, Vanessa and Chuck really do sleep together. In "Southern Gentlemen Prefer Blondes," Vanessa and Dan play the drinking game I Never, in which she admits to sleeping with Chuck twice and regretting it both times.
Georgina offers her aid in their scheme but Dan, Vanessa, and Serena reject her help, going their separate ways to find Charlie. At Chuck's hotel, Chuck saves Blair while Raina stops her father. With the police arriving, Chuck offers Blair a limo ride, and a homesick Raina breaks up with Nate, intending to return to Chicago.
In a moment of weakness, Vanessa agrees to help Chuck with a scheme having to do with Blair and Nate. Rufus learns that Dan will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education. The episode ends with Chuck and Vanessa starting a friends with benefits, and Nate and Blair starting a ...
Vanessa gets caught in the middle when Juliet sets her up for stealing Serena's phone and sending an incriminating email. Vanessa later leaves town when only Dan believes her, but tells Juliet to watch her back. [69] After Blair ran Chuck's new girlfriend out of town, he pledges war against her. [70]
[3] L.J. Gibbs, from TV Fanatic, gave the episode a 3.5 rating star out of 5, and said that he felt that Chuck being shot at the end of the episode was a very "cheap move by the writers", and that the storyline involving Chuck and Jenny having sex was very "unlikely".
Serena, Blair, Nate and Chuck decide to uncover the mysterious blogger. Chuck and Blair resolve to be vulnerable with each other after playing with each other's emotions for the past two years. Nate is contemplating a summer job in the Mayor's office as well as a summer backpacking in Europe with Vanessa.
Serena decides to come back to New York and confront Dan about the "Serena Chapter". Chuck proposes to Blair when he is implicated in the death of Bart. Georgina joins forces with Jack Bass in one last scheme to help Chuck and Blair. Nate and Sage try to find the identity of Gossip Girl with the information that they have.