Pret - A - Poor J (segunda parte)

Octavo Episodio: Pret - A - Poor J (primera parte)

Jenny (Taylor Momsen) befriends a young model, Agnes (guest star Willa Holland), who encourages Jenny to not only explore her wild side, but also confront her boss, Eleanor Waldorf (guest star Margaret Colin), who is attempting to "borrow" Jenny’s designs. Serena (Blake Lively) and Dan (Penn Badgley) agree to attend an art opening at Rufus' (Matthew Settle) gallery as friends, but the outing gets a little uncomfortable after Serena meets an artist, Aaron Rose (guest star John Patrick Amedori), and realizes they have an instant chemistry. Blair (Leighton Meester) attempts to seduce Chuck (Ed Westwick), but it proves tougher than she ever imagined.

Chuck in Real Life (segunda parte)

Septimo Episodio Chuck in Real Life (primera parte)

Vanessa (Jessica Szohr) uses the scandalous picture of Catherine and Marcus to blackmail Blair (Leighton Meester) into being a nicer person, so Blair seeks revenge by enticing Chuck (Ed Westwick) to seduce Vanessa. Lily (Kelly Rutherford) and Bart (guest star Robert John Burke) throw an extravagant housewarming party and expect their children to make them proud in front of the attending press, but a rebellious Serena (Blake Lively) isn't ready to play by their rules. Meanwhile, Dan (Penn Badgley) and Jenny (Taylor Momsen) discover a big secret that Nate (Chace Crawford) has been keeping from his friends.

New Haven Can Wait (segunda parte)

Sexto Episodio: New Haven Can Wait (primera parte)

After Blair (Leighton Meester) and Serena (Blake Lively) get into a catfight, Serena decides to get even with Blair, who has always dreamed of attending Yale, by ditching her plans to visit Brown, and instead accepting the Dean of Yale's personal invitation to visit the school. After discovering that none of his recommendation letters for Yale were ever submitted, Dan (Penn Badgley) frantically tries to figure out a way to salvage his chances of getting into the school. While on the Yale campus, Chuck (Ed Westwick) is kidnapped by a group of Skull and Bones members and Nate (Chace Crawford) hooks up with a co-ed.

Quinto Episodio: The Serena Also Rises

In the midst of Fashion Week, a furious Blair (Leighton Meester) learns that her mother, Eleanor (guest star Margaret Colin), at the suggestion of her protégé Jenny (Taylor Momsen), has given Serena (Blake Lively) and her new socialite friend, Poppy Lifton (guest star Tamara Feldman), front row seats to the Eleanor Waldorf show. Hurt once again by Serena’s popularity and her mother’s betrayal, Blair decides to sabotage the show. Meanwhile, Dan (Penn Badgley) starts hanging out with Chuck (Ed Westwick), but a walk on the dark side always has its risks and Dan learns that the hard way. Lily (Kelly Rutherford) learns a secret that her new husband, Bart (guest start Robert John Burke), has been keeping from her.