Chuck's loyalty to Nate Archibald is shown when he stops him from being taken advantage of by Carter Baizen after a Lost Weekend gone wrong (Bad News Blair).
On a constant search to gain Bart's approval, Chuck explores the option for Bass Industries to acquire the club Victrola.
In It Had To Be You, Chuck is rejected from colleges because of poor grades and is sent to military school by his father.
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.
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 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.