Cowboys receiver Roy Williams's failed proposal to Brooke Daniels went public last week when the Miss Texas USA 2009 tried to keep the $76,600 ring Williams had mailed her. (It was returned last Friday.) Perhaps both parties should have known better: Athlete-Miss pairings have a history of being mismatches.
Miss America 1955, Lee Meriwether
Rumors of nuptials flew after Joe DiMaggio's first date with one of his many Miss connections, but Meriwether (left) denied the buzz on the Today show, ending the coupling on the spot.
Miss Ohio USA 1986, Halle Berry
David Justice married the future Oscar winner in '93. The pair's divorce three years later got ugly when Berry filed a restraining order, saying she feared for her safety.
Miss Miami 1986, Esther Haddad
Jose Canseco's first marriage, to Haddad, overlapped with his dating Madonna and ended around the time Canseco rammed his Porsche into Haddad's BMW in '92.
Miss USA 1995, Shanna Moakler
The former model was engaged to Oscar de la Hoya, with whom she had a child, until she saw him with another woman at the Latin Grammys. She split, filing a $62.5 million palimony suit.
Miss Wales 2003, Imogen Thomas
The reality star caused a stir across the pond this spring when news broke of her alleged six-month affair with Man U star Ryan Giggs. The issue? He'd been married since '07.