Not satisfied with just being Queen of Constance Billard, Jenny (Taylor Momsen) sets her sights on becoming the Queen of all the Upper East Side by landing the hottest escort for Cotillion. Nate (Chace Crawford) and Chuck (Ed Westwick) plot to help Serena (Blake Lively) and Blair (Leighton Meester) repair their damaged friendship. Dan (Penn Badgley) is upset when Olivia (guest star Hilary Duff) contemplates leaving school for a movie project. Jessica Szohr, Kelly Rutherford and Matthew Settle also star. Alison McLean directed the episode written by Amanda Lasher.