The late magazine mogul's girlfriend for seven years—a majority of them as the "#1 girlfriend"—Madison was a prominent fixture in Hefner's life for nearly a decade. Having frequently visited the mansion while a 20-year-old college student in Los Angeles, the aspiring actress decided to move into the house a year later in 2001. The Oregon native, who was familiar with Playboy and had been a fan, soon became Hefner's lead girlfriend and the two appeared to fall in love.
Over the course of their seven years together, their untraditional relationship was chronicled on E!'s series, The Girls Next Door, with Madison the ever doting and loyal wife figure alongside co-stars and fellow girlfriends Kendra Wilkinson and Bridget Marquardt.