Bill Wyman

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Being the bassist for the Rolling Stones meant Bill Wyman met his share of female admirers -- even when he got old. At 52, he married 18-year-old model Mandy Smith after carrying on an affair with her for years (Scotland Yard investigated that but never charged him). What made the situation worse was when Wyman's son Stephen, 31, got engaged to Smith's 49-year-old mother. Neither relationship lasted very long, letting Bill escape the fate of becoming his own grandfather (and a lot of other weird parental roles).