Original Air Date: 28 November 2007
Although it is Thanksgiving, hardly anyone has the holiday spirit. Blair and Serena have a fight once Serena admits that she saw Blair with Chuck; Nate and his family share a strained Thanksgiving meal before Mr. Archibald ends up in the hospital after a suicide attempt; having been uninvited by Blair to the Waldorf Thanksgiving meal, the Van der Woodson family has dinner with the Humphreys and the tension between Lily, Allison, and Rufus is palpable; Blair revisits her bout of bulimia after discovering that her mother forbade her father to join them for Thanksgiving. Through the entire episode there are flashbacks of last year’s Thanksgiving. There is a stark contrast between its joy and the present’s strife.

Original Air Date: 14 November 2007
Blair is devastated by the current state of her relationship with Nate and the guilt from her recent indiscretion. But she manages to put on a happy face for her 17th birthday party and attempts to hide her feelings from her friends. Hoping to ease the tension between Serena and Vanessa, Dan takes Vanessa to Blair’s party so the girls can bond together, but this ends up making Serena more uncomfortable. Jenny brings her mother home as a surprise visit, but Rufus isn’t ready to forgive and forget. Also, Nate’s parents ask him to make a huge sacrifice to save his father’s business as he faces charges of embezzlement and fraud.

Original Air Date: 7 November 2007
Things heat up between Serena and Dan when they admit they are in love with each other, despite that they come from polar opposite worlds (she from wealthy Upper East Side Manhattan, and he from working class Brooklyn). But Serena and Dan’s plans to be alone to consummate their romance is interrupted by Vanessa who shows up wanting to spend time with Dan. Meanwhile, Chuck thinks of investing in a strip nightclub to make his father, Bart Bass, proud of him. Jenny discovers a secret that her parents have been keeping from her. Also, Blair is devastated by Nate’s actions when Jenny reveals to Blair that Nate kissed her by accident at the masked ball the night before after he mistook her for Serena. Blair, (being the cynical b*tch she is), tells Jenny they are no longer friends. Nate’s parents think that he should tell Blair he wants to marry her, even though he doesn’t have strong feelings for her. The Archibalds and Waldorf’s have a dinner party celebrating their new business deal together and it’s obvious that Blair is giving Nate the silent treatment. Nate confronts his father about the drugs he found in his house, but he denies having a problem. The two get into a brawl and Nate’s father punches him and as a result Nate turns his own father into the police. Afterwards, Nate gets ready to go see Chuck at the strip club he opened, but Blair stops him and tells him he needs to be with his father. Blair tells Nate that she doesn’t need him and they break up and she heads over to the strip club saying she wants to “escape”, which leads to a sordid tryst between Blair and Chuck in the backseat of his limousine.