Blair and Chuck continue to adjust to being in a relationship with one another. Serena returns from Europe with new secrets to hide and a new relationship.

Blair starts her first day at NYU and Georgina is assigned as her roommate. Serena recruits Carter to help her get even with Chuck.

Blair and Chuck face-off when the both set their sights on an item up for bid at Sotheby's. Serena begins to think that Carter may have returned to his old habits and Georgina becomes interested in Dan.

During the first day of school, Jenny takes her place as the new Queen Bee. Lily returns home to find that things are not as she left them. At NYU, a famous actress enrolls is assigned to be Vanessa's roommate.

Lily and Rufus decide to move up their wedding date, but complications arise. Chuck discovers a secret that Carter has been keeping from Serena. Dan and Vanessa are pulled into one of Georgina’s schemes.

Vanessa vies with Blair for the honor of delivering the freshman toast at NYU. Dan invites Olivia to meet Rufus and Lily. Serena and Nate team up to help Carter Baizen.

Chuck decides to move up his club’s opening and enlists Serena’s help, making Blair feel left out. Dan is unnerved when he watches one of Olivia’s infamous sex scenes with a former co-star.

Olivia says something she regrets on a talkshow and tries to keep Dan from finding out. Nate suspects his grandfather will stop at nothing to get Trip elected to congress.

Not satisfied with just being Queen of Constance Billard, Jenny sets her sights on becoming the Queen of all the Upper East Side. Meanwhile Dan and Vanessa try to convince Olivia to stay in NY.

Hoping to impress the elitist theater kids at NYU, Blair sets her sights on landing a private concert. Dan and Olivia sign up to write and star in a school play. Serena turns to Nate to help her get through a difficult situation.

Blair suspects her mom has been keeping a big secret from her. Jenny can’t pass up a chance to get even with Eric. Serena is put in a very awkward position when her mother invites Trip and Maureen to join them for Thanksgiving dinner.

Chuck wrestles with an issue from the past and a serious car accident rocks the Upper East Side. Dan and Vanessa attempt to navigate their newly complicated friendship.

Nate and Serena decide to explore the boundaries of their friendship. Chuck is having problems forgetting about the woman he saw at his father’s grave. Jenny agrees to help Damien.

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.

Despite being grounded, Jenny continues to see Damien. Lily tells Rufus the big secret she has been keeping from him even. Chuck is forced to make an extremely difficult decision about his hotel.

Chuck finds himself once again at odds with his uncle Jack. Eleanor puts Blair in charge of making sure her latest fashion show is a huge success. Rufus attempts to get Jenny back on track by volunteering her to help with Eleanor’s fashion show.

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.

Chuck offers to throw a wedding for a very pregnant Dorota. Serena lies to Nate about who she has plans with. Rufus discovers that Lily has been lying to him about her whereabouts.

Dr. William van der Woodsen unexpectedly shows up in Manhattan. Serena and Nate continue to have relationship issues. Meanwhile, Dan finds out that he didn’t get accepted into the Tisch writing program.

Will's return to the Upper East Side continues to stir up problems for Serena, Lily and Rufus. Serena and Jenny's relationship becomes strained. Dan learns that Vanessa has been keeping yet another secret from him.

When things get tense between Rufus and Will, Rufus is made to feel like an outsider in his own family. After many failed attempts, Chuck makes one last grand gesture to reconcile with Blair.

Blair must make a difficult decision. A Gossip Girl gossip bomb involving Dan explodes Serena and Nate's relationship. Meanwhile, Georgina returns to the Upper East Side.