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 Serena and Nate continue to have relationship issues, a scheming Jenny is more than happy to be a shoulder for Nate to lean on... Meanwhile, Dan finds out that he didn’t get accepted into the Tisch writing program and Vanessa admits she may have been somewhat responsible.

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.

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 baby. Jenny hits rock bottom. Georgina returns to the Upper East Side...and she has an agenda.