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After Marquardt left, she briefly hosted "Bridget's Sexiest Beaches" on the Travel Channel.At 86 years old, the men's magazine mogul has had more than his share of ladies — many of which he dated concurrently.And with the exception of his first wife Mildred Williams, all of Hefner's most publicized relationships were with Playboy models (and almost exclusively with blondes, as we learned).

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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.

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.

On New Year's Eve, the Playboy founder married Crystal Harris, his girlfriend of nearly four years.

VIDEO: How To Get A Beautiful Winter Blonde But this isn't Hef's first marriage, and certainly not his first long-term relationship.