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.