(Source: Getty Images)
Hugh Hefner Playboy Midsummer Night's Dream Party
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Hugh Hefner Celebrity Social Media Pics
Source: Bauer Griffin
Hugh Hefner Picture
Hugh Hefner Celebrity social network pictures.
Source: Bauer Griffin
2010 - Present
Hugh popped the question on Christmas Eve, 2010 and gave the Playmate a big diamond ring.
February 2009 - December 2010
Hugh and Crystal met on Halloween of 2008. They started dating in early 2009 and became his 'number one girlfriend...
January 2009 - January 2009
Bikini model Jenna Bentley was linked to the ultimate Playboy Hugh Hefner in 2009.

Spotted: Hugh Hefner and Wife Crystal Twerk in Miley and Robin Thicke Costumes

By Deena Bustillo on
We've gotta hand it to him: Hugh Hefner is 87 and twerks like he's no older than 67. The Playboy mogul dressed as Robin Thicke for the annual Playboy Mansion Halloween party Saturday night and, of course, his bride Crystal Harris wore a Miley Cyrus costume. Hef was almost unrecognizable without his robe for the party. Instead, he wore what looked like striped pajamas for the party — he probably couldn't quite pull off the skintight striped pants like 36-year-old Mr. Thicke did during the VMAs...Read Full Story

Hugh Hefner Finally Reveals How Many Women He's Been With

By Darrick Thomas on
(Photo: Getty Images)Being the man who started Playboy and a guy who constantly has beautiful, young women on his arm, Hugh Hefner is pretty much synonymous with sex. But how much sex has Hef actually had? Turns out, the answer is a lot, which isn't a surprise. When asked how many different women he's been with in his life, Hef told Esquire, "Over a thousand, I'm sure."What does come as a bit of a surprise is that the newly married Hef — his third marriage, this time with Playboy Playmate...Read Full Story

Crystal Harris is Auctioning Off Her Used Wedding Dress for Charity

By Deena Bustillo on
Have you ever dreamed of owning a light pink wedding dress  worn by a Playboy model while she married Hugh Hefner? Well, you're in luck! Hef's new bride, Crystal Harris, is auctioning off her gorgeous Romona Keveza gown. Harris tweeted about the auction Thursday. "I am auctioning my wedding dress with @charitybuzz to raise money for lymphoma in memory of Mary," she wrote, referring to Mary O'Connor, Hef's longtime secretary who acted more like a den mom to the gals at the Playboy Mansion over...Read Full Story

Hugh Hefner and the Girls Next Door Mourn the Death of Mansion 'Mom'

By Deena Bustillo on
Most of the stories coming out of the Playboy Mansion involve the legendary grotto, wild parties, Hugh Hefner's collection of exotic animals, and nearly naked ladies. Well, today's news is much heavier: Hef's longtime secretary and friend Mary O'Connor has died.O'Connor, who was said to be in her eighties, was featured on many episodes of E! reality show Girls Next Door. She was portrayed more like a friend and den mom than a secretary to the gals living in the mansion. O'Connor worked...Read Full Story

Hugh Hefner and Crystal Harris Prenup Details

By Deena Bustillo on
Well, for those of you who thought 26-year-old blonde Crystal Harris married 86-year-old Hugh Hefner for his money, guess again: The pair reportedly signed an "ironclad" prenup. A source (via Us Weekly) said Harris will not get a dime of her husband's $43 million fortune. Instead, his empire will go to his "children, the University of Southern California film school and a variety of charities." That's not to say that Harris won't be living like a Playmate princess while she is married to the...Read Full Story
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