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Chuck makes his first appearance in Pilot at Eleanor Waldorf's party.At the bar inside the Palace, he tries to flirt with and kiss Serena but she rejects him.
As the show opens, Chuck is shown to enjoy seducing women and who uses them to keep himself entertained when his best friend Nate or his heartless father are not around.
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.
While at her birthday party soon after, Chuck admits to having feelings for her, which she initially rejects but ultimately gives in to (Seventeen Candles).
Nate admits to Chuck later that seeing Blair happier after their breakup is causing him to miss her.
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.
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.
Jealous and still hooking up with her from time to time, Chuck schemes to keep them apart.
He gets Nate kicked out of Cotillion by manipulating him into punching Carter.
He eventually owns a dog named Monkey, a nod to the novels where he owned a monkey.