Chuck's role is initially that of an antagonist to the main characters.
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.
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.
Although he is a secondary antagonist in the original book series, the TV series elevates him to an anti-heroic main character, where he is noted for his financial ambition, hedonism and personal style.
Since they were children, Chuck has been best friends with Nate Archibald, Serena van der Woodsen and Blair Waldorf, who is his main romantic interest throughout the series.