Famous May-December Couples (VIDEO)

The public is always fascinated by May-December couples, where one partner is, shall we say a bit more mature than the other. But what are the most famous May-December relationships and how often to they work?

The one that's getting the most attention right now is Hugh Hefner's sudden announcement that he bought an engagement ring for his latest supposed girlfriend Crystal Harris. which is bringing mixed feelings from Hefner's last supposed girlfriend Holly Madison.

Madison was supposedly hopnig to have a wedding with Hefner as well so she wil be expressing those totally real not contrived for the media feelings in a televised confrontation with Hefner and his fiance. "I have a lot of different feelings on it. I don't just feel one way. I kind of didn't want to put a generic statement out there like 'Congratulations!' because I felt everyone would see through that,"

Famous May-December Couples
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It's not unusual to have mixed feelings about your ex getting married, but when matrimony is the very reason you broke up, well, it can be a little extra uncomfortable. Holly Madison said she was "very surprised" to hear Hugh Hefner recently proposed to his latest gal pal, Crystal Harris, since she and the magazine honcho split in 2008 due to his refusal to wed. Instead, 31-year-old Madison chose to share her thoughts with Hefner in person -- and with the cameras rolling for her upcoming reality show "Holly's World."

Famous May-December Couples