Elegant, sexy and stunning, she's the eldest daughter of Tripp (Donald Sutherland) and Letitia Darling (Jill Clayburgh), a thrice-married socialite who runs the family foundation. She lost her virginity to Nick and isn't shy about sharing that fact. When the series began, Karen was engaged to pro golfer Freddy Mason (Daniel Cosgrove), and she went through with a marriage ceremony, but demanded an annulment before the reception was over. A self-described loser-in-love, she looks to Nick for help in her personal life, and it seems their unresolved feelings for each other may cause a wrinkle in Nick's marriage to Lisa (Zoe McLellan). Recently she has begun seeing billionaire Simon Elder, an enemy of the Darling family, but this is only a subterfuge. Karen is actually attempting to get close to Simon to learn his plans, and she shares information she discovers with her father.