When Olivia discovers she may be forced to take a role in a new movie, she decides she needs to live the American college expeirence to it's fullest before she is forced to leave, and so her, Dan, and Vanessa decide to experience it together. But when they come to the last item on the list things get a little more heated than they originally planned. Chuck and Nate trap Serena and Blair in an elevator at Jenny's Cotillion so that they may work on their problems, and Serena finally tells Blair the truth about what she was really up to over the summer, and how she feels about her new boss Tripp. Blair insist Serena stay away from Tripp, and despite orginally agreeing with her, Serena decides instead to join him in late nights at the office. Meanwhile Jenny attempts to score the perfect date to Cotillion, but her plan may be foiled by Justin who teams up with Blair to take Jenny down.