The actress and singer met in 2003 at the Kids' Choice Awards. They broke up in 2007, but not before months of break-up and make-up, are-they or aren't-they. The nine-year age difference may have had something to do with their ultimate demise, as rumors swirled that Diaz wanted a family and Timberlake wasn't ready. Still, Diaz remains single while Timberlake quickly got another steady squeeze -- Jessica Biel.