Mandy Moore / Andy Roddick

Mandy Moore and Andy Roddick Tennis pro Andy Roddick has had trouble besting Roger Federer, but Roddick has probably spent more time in the tabloids. In the mid-2000s, he dated singer/actress Mandy Moore. The two have since split.
Genaro Molina / Los Angeles Times • Carl de Souza AFP/Getty Images
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