Chuck grew up with Upper East Side elites Nate Archibald, Blair Waldorf, and Serena van der Woodsen. He is charming and very good looking. His father is Bart Bass, an entrepreneur, a successful businessman, who made a name for himself, rather than being born into money like Chuck’s friends’ parents. Chuck is often described as the bad boy of his circle, and although he can be manipulative, we learn that he has a sensitive and caring side to him, especially for those he cares about like his best friend Nate and girlfriend and love interest - Nate's ex-girlfriend - Blair Waldorf, who is the first girl he has ever loved and the first girl he admits to loving.