Both lived in the mansion with Holly while filming the E! series for six seasons. During that time, Hugh was also dating Kendra Wilkinson and Bridget Marquardt. 1 girlfriend on The Girls Next Door, dated the Chicago native from 2001 to 2008. Holly, who was often referred to as Hugh’s No. “He was screaming at me and said it made me look old, hard and cheap.” “I came back with short hair,” Holly said, alleging the Playboy editor-in-chief was not pleased with her new look. “My hair was really long naturally, and I was just like, ‘I’m gonna go chop my hair off so I can, at least, look a little different,'” the model explained.
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