The students find out who is worthy of an early admission to Yale. Serena connects with a new Shakespeare teacher, who has no clue about what is going to happen when she gives Blair the first B grade in her life. Chuck pairs up with an unlikely ally in his battle over Bass Industries. Nate and Vanessa have a romantic night at the opera.

In the reading of Bart’s will, Chuck, Bart’s brother, Jack and Lily learn that Chuck is now the CEO of Bass Industries. Chuck agrees that Jack became his guardian. Rufus and Lily’s relationship is strained as Rufus searches for details about the child he never knew he had. Noticing the strange way his father has been acting lately, Dan does some investigating and uncovers Rufus and Lily’s secret, and he has to decide now what to do and who to tell the shocking revelation.

This episode will see Chuck having a hard time dealing with his father’s death, and runs away to Bangkok before his uncle Jack Bass brings him back to New York and to a worried Blair. While Jack tells Lily he wants to be Chuck’s legal guardian, Chuck gets in trouble in school for smoking hash. Though headmistress Queller agrees to forget the whole incident if Chuck doesn’t smoke again, Chuck lights up a joint in the office.