2x20 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.

2x19 The Grandfather

Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf existence in favor of a wild lifestyle with Carter by her side. Causing Serena and Chuck to have serious concerns about their friend and team up to take him down. 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, which causes Nate and Vanessa to have problems. In a misguided effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers. Nate and Blair have a heart to heart talk changing the way they see each other.

2x18 The Age of Dissonance

*video will be up as soon as possible, please bear with me!*

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 finds Elle and she tricks him by pretending to love him to get out of the country, then tells him to be with someone who actually cares about him. Carter Baizen also returns.

2x17 Carnal Knowledge

In retaliation for not playing by the unspoken rules of Constance Billard, Blair hatches a plan to bring down her teacher, Rachel (guest star Laura Breckenridge), and it's going to be good. After Chuck wakes up half naked on the floor in a hotel room and only has little memory of what happened the previous evening and who he was with, Nate, Serena and Vanessa try to help him fill in the missing pieces of what is turning out to be an increasingly intriguing mystery. Serena thinks Dan is sleeping with Rachel after she sees Dan brushing hair from her face.

2x16 You've Got Yale!

It's that stressful time of year when Constance Billard and St. Jude's students find out who is and isn't worthy of admission to Yale University. Serena bonds with her new Shakespeare teacher, Rachel (guest star Laura Breckenridge), who has no clue the wrath she is about to suffer after giving Blair the first B of her prep school career. Chuck pairs up with an unlikely ally in his war with Jack (guest star Desmond Harrington) over Bass Industries.

2x15 Gone with the Will

With the reading of Bart's will, Chuck, Jack and Lily learn the fate of the Bass empire. Dan's relationship with Serena is tested when Serena, along with everyone at their school find out that they share a half sibling. Blair throws a surprise party for Chuck that goes horribly wrong. Rufus and Lily's relationship is strained as Rufus seeks details about the child he never knew he had.

2x14 In The Realm of the Basses

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.