Season 1, Episode 7: “Victor/Victrola”

Originally aired: November 7, 2007
Writer: K.J. Steinberg
Director: Tony Wharmby

After surviving the on-again/off-again nature of their new relationship, Serena and Dan finally acknowledge they are crazy about each other, despite their polar opposite worlds that constantly threaten to pull them apart. Dan tries to treat Serena to a romantic evening alone. Chuck contemplates investing in a burlesque club in the hopes of making his father proud of him, only to confuse his father’s and Lily’s relationship and making Lily’s and Rufus’ relationship go further. Nate confronts his father about the cocaine he found in the house, but his father denies having a problem. Jenny discovers a secret her father, Rufus, and mother, Alison, have been keeping from her. Finally, Blair is once again devastated by Nate’s actions after Jenny reveals that Nate kissed her by accident thinking she was Serena. After Blair confronts Nate about Jenny’s confession, she breaks up with Nate as her relationship with Chuck heats up, and she loses her virginity to Chuck.