On New Year's Eve, the Playboy founder married Crystal Harris, his girlfriend of nearly four years.
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.
The ex-couple reconciled and eventually became engaged again on December 1, 2012.
Twin sisters Kristina and Karissa Shannon, aka Miss July and Miss August of 2009, were also Hefner's girlfriends during the early stages of his relationship with Harris.
(All three also appeared on the last season of "The Girls Next Door," the E!
reality series focusing on Hefner's girlfriends in the Playboy Mansion.) More recently, they were contestants on the UK reality show "Celebrity Big Brother," and eventually lost the competition on the final episode.
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.
She is currently expecting her first child with partner Pasquale Rotella.
While dating Holly Madison, Hefner was also seeing Playboy models Kendra Wilkinson and Bridget Marquardt. reality series "The Girls Next Door.") Wilkinson left the Playboy Mansion to star in her own series titled "Kendra" (and later, "Kendra On Top") with husband and football player Hank Baskett.
After Marquardt left, she briefly hosted "Bridget's Sexiest Beaches" on the Travel Channel.