The Debarted (air date: 2009-12-07) On the anniversary of Bart Bass’ death, Chuck wrestles with an issue from the past and a serious car accident rocks the Upper East Side.Dan and Vanessa attempt to navigate their newly complicated friendship.
Blair suspects her mom has been keeping a big secret from her, but it turns out to be something else entirely.
Vanessa is supposed to spend Thanksgiving with her parents, but has a fight with her mom and shows up on Dan’s doorstep.
Dan and Vanessa are pulled into one of Georgina’s schemes.
Blair is suspect of Bree and shares her concerns with Nate.
Jenny learns that Eric was behind her very public embarrassment at Cotillion and can’t pass up a chance to get even.
Serena is put in a very awkward position when her mother invites Trip and Maureen to join them for Thanksgiving dinner.The Lost Boy (air date: 2009-09-28) Blair and Chuck face-off when the both set their sights on an item up for bid at Sotheby's.Serena begins to think that Carter may have returned to his old habits, Georgina becomes interested in Dan, and Vanessa thinks that something is wrong with Scott.Enough About Eve (air date: 2009-10-19) Vanessa, hoping to finally win her mother Gabriela’s approval, desperately vies with Blair for the honor of delivering the freshman toast at NYU, but at what price?Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple. How to Succeed in Bassness (air date: 2009-10-26) In need of publicity for his new hotel, Chuck decides to move up his club’s opening and enlists Serena’s help to get the word out to her celebrity clients.Nate also returns from vacationing and brings home a mysterious girl, Bree Buckley.