Episodio Veinticuatro: Valley Girls

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In a flashback to the 80s, 17-year-old Lily Rhodes gets kicked out of boarding school and runs away to Los Angeles, reconnecting with her parents, Rick and Cece , and sister, Carol . Back in present day, Blair and Nate attend prom together, but the evening doesn't turn out exactly as planned and Chuck has a little something to do with that. Serena and Lilydon't see eye-to-eye over Serena’s recent run-in with the law.

Episodio Veintitres: The Wrath of Con

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Blair pressures Georgina into making amends for her past bad behavior by helping her in a scheme. The rivalry between Nate and Chuck over Blair comes to a head. Lily hatches a secret plan to help Rufus with Dan's college tuition.

Episodio Veintidos: Southern Gentlemen Prefer Blondes

Georgina returns to the Upper East Side after undergoing a major transformation. Chuck and Nate find themselves at a major crossroads in their relationship as it pertains to their mutual interest in Blair . Serena finds her relationship with Gabriel growing more complicated. Penn Badgley.

Episodio Veintiuno: Sender Anything

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Serena returns from her trip to Spain with Poppy and Gabriel . Blair makes a secret deal with Nate's grandfather, William , and Nate learns some disturbing information about his father's arrest. Dan takes a job as a cater-waiter to earn money for college, but is distressed when he discovers the gig is a Passover seder at the Waldorf penthouse and several of his friends and family are guests.

Episodio Veinte: Remains of the J

Serena decides to throw Jenny an intimate party for her sixteenth birthday, but things get way out of control when Poppy Lifton turns the small gathering into a huge social event. 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.

Episodio Diesinueve: The Grandfather

Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf existence in favor of a more wild and unpredictable lifestyle, causing Serena and Chuck to have serious concerns about their friend. Vanessa convinces Nate that it may be time to forgive and forget when it comes to his mother's Kennedyesque family, The Vanderbilts, who abandoned Nate and his mother when they needed them most. In a misguided effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers.

Episodio Diesiocho: The Age Of Dissonance

The Constance Billard and St. Jude seniors put on a production of "The Age of Innocence" and find their personal lives mirroring conflicts in the play. Serena develops a crush on the play's director, Julian , and enlists Vanessa's knowledge of theater to help her get the otherwise uninterested guy’s attention. Blair receives devastating news about her future that leads her on a witch-hunt for the person responsible. Dan and Rachel agree to stay away from each other in the aftermath of being discovered as more than teacher and student, but find it impossible to keep that promise. Chuck enlists help from an unlikely source, his nemesis Carter Baizen.