Gossip Girl (2007): Season 3, Episode 9

3 - 9: They Shoot Humphreys, Don't They?

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 by intentionally trapping them inside an elevator. Dan is upset when Olivia contemplates leaving school for a movie project, so he and Vanessa take her out on the town with a list of all the things that a university would make up... including a threesome. Blair and Eric plan to dethrone Jenny at Cotillion. Blair enlists Kira Abernathy (guest star Sarah Steele) to take her down and be the new queen of Constance Billard. Jonathan, upset at Eric's scheming with Blair, breaks up with him.