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Holly madison dating history

The second great creation, Hefner says, is his own life: a roller-coaster of fame, fortune and willing blondes played out against the backdrop of 10236 Charing Cross Road, the 1920s pile on the outskirts of Beverly Hills that he calls home, but which the rest of the world knows as the Playboy Mansion. And, although Hefner has never been one to blow his own trumpet, his enduring ability to perform in both the boardroom and the bedroom (even as he approaches his 83rd birthday!

) has elevated him to the status of national treasure. In recent weeks, the institution that is Hugh Hefner has been rocked by a string of public and private setbacks that have conspired to throw this elderly, somewhat deaf and increasingly frail man back into the public eye, for all the wrong reasons.

It has made Playboy, a brand that once looked cheeky and cutting-edge, seem out of touch and increasingly seedy.

••• So, as he enters old age at the Playboy Mansion, with its famous grotto, circular beds, "getting to know you" room, and walls that if they could speak would be able to fill an encyclopaedia of Hollywood misdemeanour, Hugh Marston Hefner is facing a sobering reality: his two great creations appear, after all these years, to be unravelling. The pouting face of Hefner's current troubles is Holly Madison, a former glamour model who is 28 years old, boasts measurements of 36D-23-36 (with the help of extensive surgery), and has for the past seven years lived at the Playboy Mansion as one of his official girlfriends.

The harem obeys a 9pm curfew, except on two nights a week when Hefner takes them out, always to a restaurant on one night, a nightclub the next.

At work, his magazine's profits have evaporated and its circulation is in free fall, forcing Hefner to cut back on staff - and, for the first time, to invite paying punters to his once-exclusive private parties.For any man in the public eye, this would represent a bad week.For Hefner, always a creature of habit, it has made for a bewildering upheaval in the unique domestic set-up he has enjoyed since separating from Kimberley Conrad, his second wife and mother of two of his four children, in 1999."We tried to have a baby earlier this year and it didn't work out. "He may not believe in monogamy in the traditional sense of the term, but deep down, Hef is a romantic," Watts says."What he really likes more than sex is falling in love over and over again, in a sentimental way.All, however, boil down to a single problem: Hefner's aura of Gatsby-esque sophistication is ever more at odds with his advancing years, and a changing world.The instinctive connection with the zeitgeist that was the secret of his success, and which saw him turn Playboy into one of post-war America's greatest cultural powerhouses, has apparently started to disappear.The two shared a laconic sense of humour, similar interests, and an apparent spiritual connection. In 2003, Madison was invited to move into his room (with its famous revolving bed) in a newly created role as his "No 1" girlfriend.According to Hefner, their relationship developed into a deep and genuine love affair.Last week, this cozy domestic arrangement suddenly fell apart.After weeks of frenzied speculation, on Monday Madison confirmed rumours that she had left Hefner for a younger and wealthier model, the celebrity magician Criss Angel, telling cameramen outside a Los Angeles nightclub: "Hef and I are no longer together." The revelation left Hefner deeply upset.


  1. Dating / relationship history for Holly Madison. View ShagTree to see all hookups.

  2. Let's get details about the plan for her third child and her info about her dating, wedding, TV shows, awards, bio-wiki, net worth below!

  3. Holly and Pasquale started dating in June 2011. In August 2012, Madison announced that she and boyfriend Pasquale Rotella were expecting their first child together.

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