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.

2x13 O Brother, Where Bart Thou?

A sudden and tragic event has an on impact on the lives of our favorite Upper East Side teens and their parents.

2x12 It's a Wonderful Lie

For the annual Snowflake Ball, Blair and Chuck make a bet that they can find the ideal dates for each other but end up dancing with one another in the end. Aaron’s ex-girlfriend, Lexi (guest star Natalie Knepp), expresses an interest in Dan which creates conflicted feelings for Serena. Nate, Jenny and Vanessa get into a tangled situation that puts their friendships and hearts on the line. Lily and Rufus also end up dancing with each other at the Ball, also. But all problems are put on hold when it is discovered that a loved one's life has been claimed.

2x11 The Magnificent Archibalds

Thanksgiving on the Upper East Side. Thanksgiving in the Waldorf household finds Blair upset that her mom's new boyfriend Cyrus, has decided to ruin all her favorite traditions. Lily finds herself trying to broker a peace treaty between Rufus and Jenny, who is prepared to cut off all communication with her father if she doesn't get her way. Serena isn't quite ready to come clean with Aaron about her complicated past, but Dan ends up accidentally revealing a few tidbits of his own. Vanessa and Chuck come to their friend's aid when Nate is once again forced to confront his father's abandonment, as he finally returns from abroad. Vanessa becomes depressed upon hearing that Nate is leaving New York with his father, but she doesn't hear that from Nate himself. Finally, Eric discovers a secret that Bart has been keeping from Lily.