The Girls Next Door was an E! Network show following life of Madison and others at the Playboy Mansion.

Madison with then-boyfriend Hugh Hefner in 2008 Madison was later among the former Playmates who spoke out in the docuseries Secrets of Playboy. Hefner confirmed the breakup, saying, 'If Holly says it's over, I guess it's over'. On October 7, 2008, Madison announced that her relationship with Hefner had ended, but that she, Bridget Marquardt and Kendra Wilkinson were 'still filming stuff together'. It's not a personal thing I just haven't had much luck with marriages.' Reflecting on her time at the mansion, Madison has said her feelings for Hefner were attributable to Stockholm syndrome. However, in an interview at the Playmate of the Year luncheon in May 2008, Hefner said, '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. During her time with Hefner, Madison stated that she wanted to marry him and have his children. In February 2002, after all but two of his girlfriends left, Madison became his '#1 Girl'.

Hefner controlled her finances, enforced a strict schedule and curfew, and denied her opportunities to earn income outside the mansion. Career Relationship with Hugh Hefner and Playboy įacing credit card debt and potential homelessness, in August 2001, Madison moved into the Playboy Mansion and officially became one of Hugh Hefner's girlfriends. Her appearance at those venues led to invitations to the Playboy Mansion and, at the age of 21, after more than a year of such visits, Madison asked permission from Hugh Hefner and was eventually allowed to move in at the mansion. To afford her college tuition, Madison competed to become a Hawaiian Tropic model and worked as a waitress at Hooters. Afterward, Madison moved to Los Angeles and attended Loyola Marymount University. She later attended Portland State University for two years, majoring in theater and psychology. When she was in middle school, her family returned to St. At age two, she moved with her family to Craig, Alaska, on Prince of Wales Island. Madison was born Holly Sue Cullen in Astoria, Oregon. She has released two books, Down the Rabbit Hole in 2015, about her life in the Playboy Mansion and her relationship with Hefner, and The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention in 2016. She also starred in her own reality series, Holly's World, which ran from 2009 to 2011. Holly Madison (born Holly Sue Cullen December 23, 1979) is an American television personality, best known as a former girlfriend of Hugh Hefner and for her appearance in the reality television show The Girls Next Door.

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