An anonymous Gossip Girl blast starts a very damaging rumor about one of Columbia's new students, Serena. On her path to greatness, Blair decides to take a class with a powerful businesswoman, Martha, who is guest-lecturing at Columbia, but a mysterious fellow student thwarts her plans to secure the prized position as Martha's assistant.
Nate suspects that Juliet is keeping a big secret from him and decides to confront her. Blair schemes to undermine Chuck's newfound happiness. Dan finds himself torn between his feelings for Serena and Vanessa.
Silver, Naomi and Adrianna craft a plan to seduce Mr. Cannon and prove that he raped Naomi, but they underestimate his ability to control the situation. Teddy and Ian are forced to do manual labor as punishment for fighting. Dixon fears for his life and pushes Ivy away, leading her straight into the arms of Oscar. A pregnant Jen seeks to hire a new assistant and Debbie applies for the job.
Silver plans a cancer-awareness charity event to honor her mother and enlists the help of Navid, Dixon, Liam and Teddy to appear in a bachelor auction. Ian, a theater student at West Bev, is brought in to help choreograph a dance number for the auction, but all comes to a stand-still when Teddy directs some negative words toward him. Annie and Adrianna discover the truth about Naomi and Mr. Cannon. Annie discovers Debbie's financial problems and decides to take an offer to make some quick cash. Ivy and Dixon decide to spend the night together, but Dixon hits the brakes when Sasha returns with some life-altering news.
Naomi has constant flashbacks to her rape and begins taking sleeping pills in order to sleep through the night. Mr. Cannon invites Silver over to his apartment to watch his new documentary and secretly slips something in her drink. Meanwhile, Teddy wakes up from a night of drinking and realizes he hooked up with someone. Dixon learns that, despite what he assumed, Ivy is a virgin. Annie confronts her boss, Katherine about her awkward behavior and is shocked when she makes her an offer she may not be able to refuse. Adrianna sings a new stolen song at a memorial service but she soon regrets her decision to do so when the video goes viral on the web.
On her first day at Columbia, Blair attempts to gain membership into an ultra-exclusive social club, Hamilton House, but she's in for a few big surprises. Serena begins to suspect that Juliet is intentionally sabotaging Serena's life and that it may have something to do with Nate. Rufus is worried about Dan and decides to take matters into his own hands.