iographies, profiles, and interviews suggest the answer is: probably pretty boring. Hefner has been married twice before—in 1949 to high-school classmate Millie Williams, with whom he had two children, and in 1989 to Playmate Kimberley Conrad, with whom he had two more.The Playboy mansion comes across not so much a prison as a singularly unsexy place of strict routines, tight curfews, and old movies. His marriage to Williams lasted 10 years, and according to University of Missouri historian Steven Watts was undone by a basic incompatibility as well as by Hef's open dalliances with other women. While the relationship between Hef and his ladies is dramatically different from the plural relationships we have grown accustomed to seeing ( After running circles with the commitment-phobic Hefner for years, Holly decided to call their relationship quits. broke the mold with this hit reality series that helped pave the way for plural relationships to become a part of mainstream media.But luckily for Hef, either Karissa or Kristina has a small mark on her neck that helps him crack the bombshell code. Or is the world's most legendary bachelor just getting that old?Maybe it's the age difference; we know we can't always tell friends' babies apart, and there's a much shorter time span between us and newborns and Hef and his babes.In 2010, she announced a pilot for a new reality show on E!but later said the network decided not to pick up the show.
In 2013, Holly’s personal dreams came true when she and her then fiancé Pasquale Rotella welcomed their first child Rainbow Aurora lasted just one season.
This long list of lovers and exes covers an entire lifespan yet the women seem to always be young.
One of many famous celebs who married much younger women, Hugh Hefner has only been married a couple times but he's dated continuously.
had run a piece describing the Mansion as a "squalid prison" run by a controlling senior citizen who, amid decaying surroundings, doled out weekly allowances to his girlfriends and kept sex parties tightly scheduled.
The story borrowed heavily from a four-year-old tell-all written by a disgruntled former girlfriend named Izabella St. Still, it's enough to make one wonder: What must it be like to be married to Hugh Hefner?