READ: Why EVERYONE Should Get a Prenup Check out some of the ladies who have won Hef's heart.
Hefner's current girl, new wife Crystal Harris, was Playboy's Playmate of the Month in December 2009. Five days before their initial wedding date of June 18, 2011, Harris called off the nuptials.
Former Playboy model and original "Girls Next Door" star Holly Madison was involved with Hefner from 2003 through 2008.
Afterward, Madison starred in a short-lived reality series called "Holly's World," which chronicled her life in Las Vegas.
After Marquardt left, she briefly hosted "Bridget's Sexiest Beaches" on the Travel Channel.