Chuck has a lot of money, but he doesn’t have a mother. She died giving birth to him, which is the sort of poignant, tragic detail you would not associate with Chuck, the Upper East Side’s ultimate bad boy. Chuck’s best friend is Nate Archibald, whom he regularly betrays. Nate always forgives him. In Season 1, Chuck’s Dad, Bartholomew, is a supporting character. He gives Chuck a lot of headaches and a lot of money. Then Bart dies, leaving his widow, Lily van der Woodsen Bass (Serena’s mother) as wealthy as Chuck. Chuck does not squander money. He spends it on things he needs: limos, private planes to Europe, hand-crafted suits, the best restaurants, the best hotels. The best women. In the GG books, Chuck was bi-sexual but not on TV. Chuck prefers the ladies, and plenty of ‘em. His fave is Blair Waldorf, who is as scheming and conniving as he is. Despite the fact that they are clearly soul mates, his and Blair’s romance is so off-again, on-again it might as well be an environmentally friendly light bulb.