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As Bart Bass and Lily van der Woodsen's relationship progresses, they decide to move their families in together.
Chuck and Eric van der Woodsen, Lily's son and Serena's younger brother, become especially close.
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.
In episode seven, "Victor/Victrola", Chuck purchases a burlesque club, Victrola.
After Nate and Blair break up, Blair visits Chuck at Victrola where she ends up performing on stage.
Lazy, and vain, Chuck's only interests are sex and money, and he is frequently chided by his father for lacking ambition and performing poorly in school.
Following flings with numerous females and males, his only serious relationship comes near the end of the series, when he begins dating Blair Waldorf, a self-obsessed, luxury loving teenager.
His father is Bart Bass, a self-made billionaire, which is irregular, compared to the Bass' old money friends.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.