Lily has been married more often than Henry VIII, and some of her husbands are dead, though none by decapitation. One, Bartholomew Bass, father of Chuck, was a billionaire who left her set for life, with no worries about bills from Tiffany's and Bergdorf's. Lily, a former ballerina, is very concerned with social status—the main reason she is at first reluctant to admit to having been a groupie when Rufus Humphrey was a rock star. They even had a secret love child. Lily's children, Serena and Eric, roll their eyes a lot. They find out about their mother's secret love child in Season 2, but heads will spin when they encounter him in the flesh in Season 3. Lily and Rufus get engaged at the end of Season 2.