Fourplay
Playboy founder Hugh Hefner finds himself with not one, not two, but three girlfriends simultaneously in the form of Holly Madison, Bridget Marquardt and Kendra Wilkinson. The unique arrangement becomes the basis for the hit E! show The Girls Next Door in 2005.
Having Your Cake and Eating It, Too
Holly, Bridget and Kendra cozy up to their man in April 2008 to celebrate his 82nd birthday.
Moving Out and Moving On
All three gals eventually part ways with Hugh in 2008 and decide to leave the Playboy mansion, although many believe he and Holly are meant to be together forever.
One For the Wedding Album
Hugh shares a moment with Kendra just before his ex and Hank Baskett tie the knot at the mansion.
Sharing the Wealth Yet Again
Hugh acquires three new girlfriends—Crystal Harris and twins Kristina and Karissa Shannon—who move into his pad in October 2008.
Holiday Hotness
'Tis the season to be...topless? Hugh's 2008 Christmas card featuring Karissa and Kristina is nothing short of titillating.
Putting a Ring On It
The twins move on and it's Crystal who Hugh ends up popping the question to on Christmas Day in 2010.
Out With the Old, In With the New
The engaged duo celebrates the arrival of 2011, the year of their supposed nuptials.
The Center Folds
Hugh tweets on June 14 that "the wedding is off. Crystal had a change of heart." On her blog, the onetime bride-to-be wrote: "After much deep reflection and thought, I have decided to end my engagement with Hef. I have the utmost respect for Hef and wish him the best going forward."