The book begins with Blair Waldorf and Serena van der Woodsen at a Black And White charity ball, hosted by rock star, Flow. Blair is angry after being dumped by Nate Archibald in favor of Jenny Humphrey. Serena catches the attention of Flow, and, after being asked by Aaron Rose's best friend, Miles, to go on to a new nightclub, she strikes up much speculation as to her relationship with Flow. Blair has written a college admissions essay, based on Audrey Hepburn, but it is denied by her guidance counselor, Mrs. Glos. Blair has naturally invited Serena to her winter vacation to St. Barts, much to the envy of her classmates, and sets off, expecting to complete her essay whilst there. Aaron has developed feelings for Blair, and he starts to fall in love with her, but his friend Miles has already got Blair's attention. Blair's mother announces that she is pregnant with her third child, with Cyrus Rose. Serena receives large and strange gifts from Flow, Kati and Isabel, including a talking parrot and a bowl full of baby barracudas. Blair has decided to lose her virginity to Miles, and almost does, until Aaron disturbs them. Blair is obviously furious, and asks Serena to leave with her to go back to New York on Christmas Day. Whilst Blair completes her college application, Serena organizes a huge New Years Eve party. Meanwhile, Nate and Jenny's relationship is still strong, and are accidentally filmed in the park, fooling around, by Vanessa Abrams. However, Nate soon realizes how much he missed Blair, and, after realizing Jenny's obsessiveness towards him, decides to break the relationship off, unknown to Jenny. Because of the link (accidental filmed by Vanessa), Dan and Vanessa didn't communicate with each other until the New Years eve when Dan decided to talk to Vanessa after receiving a letter from The New Yorker newspaper that his poem will be published next month. Vanessa mailed the poem to the New Yorker even though the poem is about her entitled Slut, she was convinced that the poem has its depth words in it. On the other hand, Vanessa's work on the link spread all over the town was also recognized by Ken Mogul, a known filmaker, who wanted to work with her.
