10 of 61:
Hugh Hefner, founder of Playboy magazine, and Playmate Crystal Harris, became engaged on Christmas Eve, Dec. 24, 2010. At the time, he was 84 and she was 24. The two have been linked since at least 2009. They planned on marrying on June 18, 2011 but Hefner said on his Twitter page on June 14: 'The wedding is off. Crystal has had a change of heart.'
(Pictured: Hugh Hefner and Crystal Harris appear in a photo posted on his Twitter page in June 2010.)