Hugh Hefner and Kimberly Conrad Hugh Hefner and Kimberly Conrad

Though Hugh Hefner has had many girlfriends over the years, Kimberley Conrad is one of only two women to get the original Playboy to settle down. However, after 11 years of separation, Hefner has filed for divorce from his second wife.

Hefner, 83, cited irreconcilable differences with Conrad on Friday when filing the papers, according to People.com. The couple married in late 1989.

Conrad, 47, who had long since lived in a home next to the mansion, is also the mother of two of Hefner's children, Marston, 19, and Cooper, 18. Hefner's first wife, Mildred Williams, is the mother of his two eldest children, Christie and David Hefner.

Calls to Hefner's reps were not immediately returned.