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06 Feb

This leads Chuck to have a temporary rift with both Blair and Nate.

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.

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.

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.Chuck is often described as the "bad boy of his circle." Chuck is a playboy and womanizer who sees women as recreational tools. 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.Chuck's role is initially that of an antagonist to the main characters.