Hiro attempts to delve into Arthur Petrelli’s past to uncover the mystery behind him creating a rival company Pinehearst and his hatred towards Angela. Sylar stricken by guilt tries to stop his murderous ways with HRG and Elle vying for his blood. Meredith’s training goes up in smoke with the arrival of her brother.

Serena invites Aaron to be her guest at a charity gala honoring Lily and Bart, but after discovering a secret that Aaron has been keeping from her she begins to question whether Aaron is the guy she thought he was. Hoping it will help her chances of getting into Yale, Blair naively agrees to babysit the 15-year-old daughter of a prominent Yale donor, but the teenager proves to be more than a handful and Blair begins to suspect that the evening may actually wind up hurting her chances of getting into college of her dreams. Meanwhile, Jenny and Agnes plan a guerilla fashion show that will either launch Jenny’s star or ruin her chances of ever being accepted by the industry.

Jenny has a new young model friend, Agnes, who encourages Jenny to explore her wild side, and also to confront, Eleanor Waldorf, who is attempting to “borrow” Jenny’s designs. Meanwhile Serena and Dan attend Rufus art opening as friends, but then Serena meets an artist, Aaron Rose, and the evening gets a little uncomfortable. Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined.

Vanessa tries to blackmail Blair into being a nicer person, with the pictures of Catherine and Marcus. Blair then seeks revenge by convincing Chuck to try to seduce Vanessa. Lily and Bart throw an extravagant housewarming party and expect their children to make them proud, but Serena do not want to follow the rules. Meanwhile, Dan and Jenny discover a big secret that Nate has been keeping from his friends.

Blair, Serena, Dan, Nate and Chuck go to Yale. After Blair and Serena get into a fight, Serena decides to get even with Blair, who has always dreamed of going to Yale, by going to Yale instead of going to Brown as planned and accepting the Dean of Yales private invitation to the campus. Dan discovers that none of his recommendation letters for Yale were sent, he tries to figure out a way of getting into the school. Also Chuck is kidnapped by a group of Skull and Bones members and Nate hooks up with a co-ed.