How long has Hugh Hefner been seeing Holly Madison?

No, Hugh Hefner was married from 1989 to 2010 to Playboy centerfold Kimberley Conrad, with whom he had two children. Madison and Hefner ended their relationship in 2008. After Hefner and Conrad divorced, he married Crystal Harris in 2012. Holly Madison is expecting a second child in 2016 with husband Pasquale Rotella.