Blair has to decide between meeting Chuck at the Empire State Building or risking their future together. A gossip about Dan causes problems for Serena and Nate. Meanwhile, Georgina Sparks (Michelle Trachtenberg) returns to the Upper East Side with and agenda.

When things get tense between Rufus and Will, Serena chooses to stand behind her father, while at the Rufus is made to feel like an outsider in his own family. Meanwhile, Jenny deliberately shares information with Will that may ultimately destroy Lily and Rufus’ marriage. After many failed attempts, Chuck makes one last grand gesture [...]

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 Columbia campus and realizes where she truly belongs…. Dan learns that Vanessa has been keeping yet another secret [...]

Serena’s father (William Baldwin) visits Manhattan unexpectedly; Nate and Serena continue to have relationship issues; Dan gets upsetting news.

Jack Bass is back in NY and Chuck finds himself at odds with his uncle. Eleanor puts Blair in charge of making sure her fashion show is a huge success with an important client. Rufus tries to get Jenny to be more good by volunteering to help in Eleanor’s fashion show, but it takes a [...]

Despite being grounded, Jenny continues to see Damien who pressures her to sleep with him. Lily tells Rufus the big secret she has been keeping from him even though she knows it’s very risky. Meanwhile, Dan and Vanessa explore the new stage of their friendship, while Chuck is forced to make a very difficult desicion [...]

Rufus and Lily suspect something bad about Jenny’s and Damien relationship. Chuck learns more about the woman at the cementery who may or may not be his mother. Meanwhile, Dan and Vanessa struggle with the awkwardness of dating other people.

Nate and Serena explore their friendship. Blair thinks Chuck is having problems forgetting the woman he saw at his father’s grave. Jenny go with Damien to a State Dinner but she wasn’t aware that it was also to help him with a drug exchange. Vanessa and Dan try to move past Dan’s confession. Rufus returns [...]