Episode 1 | Reversals of Fortune

Blair and Chuck adjust to their new status as a couple; Serena returns from Europe with many secrets and a complicated relationship with Carter.

Episode 2 | The Freshmen

Blair begins NYU, determined to keep her Queen Bee status, but Georgina has other ideas; Serena recruits Carter to get even with Chuck.

Episode 3 | The Lost Boy

It's Blair versus Chuck as they both set their sights on a particular item up for bid at Sotheby's; Georgina takes an interest in Dan.

Episode 4 | Dan de Fleurette

It's Jenny's first day as Queen Bee; A famous actress, Olivia Burke, is assigned as Vanessa's roommate.

Episode 5 | Rufus Getting Married

Lily and Rufus move up their wedding, but complications threaten to tear them apart; Chuck discovers a secret Carter has been keeping from Serena; Dan and Vanessa are pulled into one of Georgina's schemes.

Episode 6 | Enough About Eve

Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple; Serena and Nate team up to help Carter Baizen.

Episode 7 | How to Succeed in Bassness

Serena helps Chuck open his club, but Blair feels left out; Dan is unnerved watching one of Olivia's sex scenes with a former co-star.

Episode 8 | The Grandfather: Part II

Olivia says something she regrets during a talk show appearance and tries to keep Dan from finding out; Nate suspects that his grandfather will stop at nothing to get Trip elected to congress.

Episode 9 | They Shoot Humphreys, Don't They?

Jenny sets her sights on landing the hottest escort for Cotillion. Dan is upset when Olivia (HILARY DUFF) contemplates leaving school. All-girl French band PLASTISCINES performs.

Episode 10 | The Last Days of Disco Stick

Dan and Olivia sign up to write and star in a school play, based on an idea by Blair and directed by Vanessa.

Episode 11 | The Treasure of Serena Madre

Serena is put in an awkward position when Lily invites Tripp and Maureen to join them for dinner; Blair suspects her mother of keeping a big secret; Jenny gets even with Eric in the most cruel way.

Episode 12 | The Debarted

Chuck wrestles with a past issue; A serious car accident rocks the Upper East Side; Dan and Vanessa try to navigate their complicated friendship.

Episode 13 | The Hurt Locket

Chuck tracks the woman he saw at his father's grave; Jenny agrees to help Damien; Nate and Serena get friendly.

Episode 14 | The Lady Vanished

Rufus and Lily grow suspect of Jenny's relationship with Damien. Chuck learns more about the woman who may or may not be his mother. Dan and Vanessa struggle through the awkwardness of dating other people.

Episode 15 | The Sixteen Year Old Virgin

Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have sex with her. Lily thinks to tell the secret that she has up till now concealed, but after a call, she changes her mind. Dan and Vanessa e...

Episode 16 | The Empire Strikes Jack

Chuck finds himself once again at odds with his uncle, Jack Bass. Eleanor puts Blair in charge of making sure her latest fashion show is a huge success with an important client. Rufus attempts to get Jenny back on track by volunte...

Episode 17 | Inglourious Bassterds

Chuck and Blair are faced with the most difficult decision they have ever faced as a couple. Serena plans a surprise birthday party for Nate, but Jenny does her best to sabotage Serenas's efforts. Dan and Vanessa's new relationshi...

Episode 18 | The Unblairable Lightness of Being

Chuck offers to throw a wedding for a very pregnant Dorota who insists that she and Vanya have a traditional wedding before her parents arrive from Poland and find their daughter pregnant and without a husband. Dorota asks Blair a...

Episode 19 | Dr. Estrangeloved

When Lily's ex-husband, Dr. William van der Woodsen, shows up unexpectedly in Manhattan, Serena finally gets the reunion she has so desperately wanted with her father, but the circumstances turn out to be far from ideal. When Sere...

Episode 20 | It's a Dad, Dad, Dad, Dad World

Will's return to the Upper East Side continues to stir up problems for Serena, Lily and his long-standing rival, Rufus. Serena and Jenny's relationship is strained as a result of Jenny's deception. Blair spends time on the Columbi...

Episode 21 | Ex-Husbands and Wives

When things get tense between Rufus and Will, Serena chooses to stand behind her father, while Rufus is made to feel like an outsider in his own family. Meanwhile, Jenny deliberately shares information with Will that may ultimatel...

Episode 22 | Last Tango, Then Paris

Blair must decide whether to meet Chuck at the top of the Empire State Building or risk losing their future together. A Gossip Girl gossip bomb involving Dan explodes Serena and Nate's relationship. Dorota and Vanya welcome their ...