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 to reconcile with Blair, hoping she will finally accept the fact that they are destined to be together.

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 from him.

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

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 and Chuck to be part of the ceremony and walk her down the aisle. Serena tells Nate she is having breakfast with the Humphreys when in reality she’s secretly meeting up with Carter Baizen. Rufus discovers that Lily has been lying to him about her whereabouts.

Blair and Chuck face a difficult decision that tests their relationship; Jenny tries to sabotage Serena’s efforts to plan a surprise party for Nate.

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 volunteering to have her help with Eleanorfs fashion show, but the opportunity takes a big turn for the worse when Jenny learns that Agnes will be one of the models.

Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have sex with her. Lily tells Rufus the big secret she has been keeping from him even though she knows it’s a huge risk. Dan and Vanessaexplore a new stage of their friendship. Chuck is forced to make an extremely difficult decision about his hotel.

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.

Nate and Serena decide to explore the boundaries of their friendship. Blair suspects that Chuck is having problems forgetting about the woman he saw at his father’s grave. Jenny agrees to accompany Damien to a State Dinner but is unaware that he needs her help with a drug exchange. Vanessa and Dan attempt to move past the awkwardness of Dan’s confession of love. Rufus returns from a ski trip and tries his best to avoid Lily.<object width=”640″ height=”344″><param name=”movie” value=”http://www.megavideo.com/v/WUCUD32Hee3bde3b86dc5c64be038bca0de445e8″></param><param name=”allowFullScreen” value=”true”></param><embed src=”http://www.megavideo.com/v/WUCUD32Hee3bde3b86dc5c64be038bca0de445e8″ type=”application/x-shockwave-flash” allowfullscreen=”true” width=”640″ height=”344″></embed></object>