At Blair's Kiss on the Lips party, he meets Jenny Humphrey and attempts to rape her.
However, he is stopped by Dan Humphrey, who punches him.
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 series progresses, Chuck becomes a more compassionate and mature character; he undergoes one of the deepest growths in a character on the show.
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.
Chuck is orphaned in his senior year at high school due to the death of his father in a car accident, before being adopted by Lily van der Woodsen, his stepmother, and the only parent who Chuck really connected to and loved unconditionally.