<P> Constance Billiard School is an exaggerated version of Gossip Girl author Cecily von Ziegesar's alma mater, the Nightingale - Bamford School . It was revealed in preparation for the 2007 TV series debut, Josh Schwartz hired recent graduates of Ziegesar's alma mater to retool several characters . </P> <P> Chuck Bass was then reconfigured as a more central character, an antiheroic playboy whose on - off relationship with Blair Waldorf serves as one of the show's major ongoing storylines . Chuck is the resident "bad boy" of the Upper East Side, and like Blair, is both vengeful and manipulative; the two often scheme elaborate plans together . As the show progresses, Chuck develops a softer side, specifically towards Lily, Eric, and Serena, his adoptive mother, brother, and sister . </P> <P> Chuck grew up on the Upper East Side with his three best friends and fellow elites Nate Archibald, Blair Waldorf, and future - stepsister Serena van der Woodsen . His father is Bart Bass, a self - made billionaire, which is irregular, compared to the Bass' old money friends . Chuck is often described as the "bad boy of his circle ." Chuck is a playboy and womanizer who sees women as recreational tools . Chuck frequently skips class and smokes cannabis . </P> <P> In the pilot episode, Chuck attempts to rape both Serena and Jenny Humphrey . When speaking about Serena in the pilot episode, Chuck says, "Serena looked effin' hot last night . There's something wrong with that level of perfection . It needs to be violated ." With time, he attenuates his behaviors as a sexual predator and becomes more of a manipulating womanizer, however, his lecherous attitude continues as he makes multiple advances on his step - sister at the time, Serena . </P>

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