As a result of Georgina (guest star Michelle Trachtenberg) revealing the true reason that Serena (Blake Lively) fled Manhattan for boarding school, Serena falls back into her old habits and Blair (Leighton Meester), Nate (Chace Crawford) and Chuck (Ed Westwick) must put their complicated feelings for each other aside to help their friend. Unfortunately, Serena is too ashamed to share the truth with Dan (Penn Badgley), leaving him only to assume the worse about his girlfriend.
Rufus (Matthew Settle) is thrilled when his band is invited to perform at a Rolling Stone-sponsored concert, but Lily (Kelly Rutherford) is the last person on earth he expects to see at the performance, especially since her wedding rehearsal dinner is the same night. Lisa Loeb and famous cake designer Sylvia Weinstock appear in the episode as themselves. Jessica Szohr also stars.