It's that stressful time of year when Constance Billard and St. Jude's students find out who is and isn't worthy of early admission to Yale University. Serena (Blake Lively) bonds with her new Shakespeare teacher, Rachel (guest star Laura Breckenridge), who has no clue the wrath she is about to suffer after giving Blair (Leighton Meester) the first B of her prep school career. Chuck (Ed Westwick) pairs up with an unlikely ally in his war with Jack (guest star Desmond Harrington) over Bass Industries. Nate (Chace Crawford) and Vanessa (Jessica Szohr) spend a romantic evening at the opera.