Hugh's former long-term girlfriend is angry and confused about why she wasn't given a ring.
By K Maine — Written on Dec 28, 2010
No one can argue that Holly Madison didn’t put in her time with Hugh Hefner. She was his devoted girlfriend and loyal arm ornament at red carpet events 2001 to 2008. The couple was together for seven years (although never entirely exclusive) and Holly was always depicted on The Girls Next Door as Hugh’s main lady—she was a sort of house mother to Hugh’s other girlfriends; the leader of the pack.
So it’s not surprising that Celebitchy is reporting that Holly was very pissed to learn about Hef’s engagement to the young wisp of a woman, Cyrstal Harris, who, at 24, is seven years younger than Holly. Hugh Hefner Gets Engaged To Playmate Crystal Harris
Holly has said before that she always wanted to marry Hefner and have his children. She clearly was hoping to secure herself financially to the old man, who is worth approximately $40 million. As a live-in girlfriend, Holly's rent was paid by Hugh and she was given a salary. But it seems she wanted more of a guaranteed income than that.
After their breakup, Holly admitted that she had been trying to get pregnant with Hugh’s child while they were together, and when she wasn’t having any luck, she reportedly began funding her own IVF treatments. But Hugh was never willing to pop the question to Holly, and there was talk that Hugh’s sperm count was running dry at the time of their breakup. During an interview at the Playmate of the Year luncheon in May 2008, Hefner stated, “I love Holly very much and I think we’re going to be together the rest of my life, but marriage isn’t part of my puzzle. It’s not a personal thing; I just haven’t had much luck with marriages.” Holly Madison: Out of the Mansion
Hugh Hefner is currently 84 years old and has been married twice before his engagement to Cyrstal. His first marriage lasted ten years (1949 to 1959) before divorce; the union existed a few years prior to the launch of Playboy and beget two children. They apparently divorced because his wife was unfaithful, and it broke Hugh's heart. Hugh didn’t remarry for thirty years, when he wed one of the magazine’s playmates, Kimberley Conrad. The couple had two children together, and although they officially remained married until 2010, they separated back in 1999, and Conrad lived next door to the Mansion. Hugh has stated that the couple only remained married for their children’s sake.
Following her breakup from Hugh, Madison began dating illusionist Criss Angel, but they broke up three months later. Madison told People magazine in March 2009, "I'm never dating anybody again. I don't need a man. I'm really happy with myself and being with my friends." Still, after this statement, Holly briefly dated Good Charlotte guitarist Benji Madden and guitarist Jack Barakat. She was interviewed on December 9, 2010, stating "It’s just a case of having fun together and not thinking about the future.”