Jenny has a new young model friend, named Agnes, who encourages Jenny to explore her wild side, and also to confront Eleanor Waldorf who is planning to steal Jenny's designs in order to pass them off as her own. Meanwhile, Serena and Dan attend Rufus' latest art opening as friends, but then Serena meets an artist, named Aaron Rose, and the evening gets a little uncomfortable for Dan. Elsewhere, Blair attempts to seduce Chuck, but he proves to be tougher than she ever imagined. Also, Jenny begins to have a mutual feelings with Nate as he's staying with her, Dan, and Rufus while searching for a place to live.

Serena invites Aaron to a charity event, but soon uncovers a secret Aaron has been keeping from her. Thinking it will help her get into Yale, Blair agrees to babysit the 15-year-old daughter of a Yale donor, but her plan quickly backfires. Meanwhile, Jenny and Agnes plan a fashion show.

Blair sets out on a mission to break up her mother and Cyrus Rose, her new man. Jenny moves in with Agnes as the two continue with their plans for their own fashion line. As Serena continues to fall for Aaron, she learns something that may derail their relationship forever while Dan interviews Bart Bass for an article for New York Magazine.

It's Thanksgiving time and Blair is offended when her Mom's new man hijacks her Thanksgiving traditions. Lily attempts to strengthen the frail bond between Rufus and Jenny. Eric discovers a secret about Bart. Vanessa and Chuck help Nate deal with his father.

At the Snowflake dance, Blair and Chuck discover their lookalikes hooking up. Aaron's ex Lexi flirts with Dan, causing trouble with Serena. Nate, Jenny and Vanessa get into a messy love triangle that involves a stolen letter and a revealing dress. Bart Bass suffers a car accident on his way to the ball.

The entire Upper East Side of Manhattan is rocked when Bart Bass dies suddenly in a limo accident. Serena and Eric take the news very calmly while Lily has a troubling time despite her mother, Cece's, awkward attempts to comfort her. Chuck begins to blame Lily for his father's death and threatens to reveal a secret that Bart found on her before his accident. Meanwhile, Blair's mother, Eleanor, prepares for her latest marriage to Aaron's father Cyrus.