Not satisfied with just being Queen of Constance Billard, Jenny sets her sights on becoming the Queen of all the Upper East Side by landing the hottest escort for Cotillion. Meanwhile, Nate and Chuck plot to help Serena and Blair repair their damaged friendship. Dan is upset when Olivia contemplates leaving school for a movie project, so he and Vanessa take her out on the town with a bucket list. Blair and Eric plan to dethrone Jenny at Cotillion, so they enlist a student at Constance to take her down.