Holly Madison is the Number One girlfriend of Hugh Hefner. He confessed that Holly was the true love of his love. Hugh had some legal complications as he was still legally married to Kimberly Conrad. With countless women at his beck and call, Hugh was terribly spoilt for choice. Holly’s lovely personality shone through and since 2001, she has remained as Hugh’s favorite girlfriend. Holly may pretend to be eating ice cream here but in reality, I doubt if she could really eat ice cream. Her life and career depended on looking beautiful.