![]() Matthew Settle as Rufus Humphrey, Dan and Jenny's father.Her and Serena often have a strained and rocky relationship. ![]() A former photographer, Lily has become one of the UES's most influential socialites. Kelly Rutherford as Lily van der Woodsen (née Rhodes), Serena's and Eric's mother and a three-time divorcée.Blair and Chuck's relationship is a key theme throughout all 6 seasons. He is romantically involved with Blair throughout the series but they do not start officially dating until the third season. Once his father dies in the second season, he inherits Bass Industries and becomes a young billionaire. Decadent and amoral, Chuck is mainly interested in women and alcohol. Son of one of New York's most successful real estate moguls. ![]()
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