penthouse . having established himself in chicago bulls chicago chicago he moved out west and made his permanent home in los angeles. in 1949 married playboy of the year kimberly conrad the couple had two children and separated in 1998 he realized he is much happier as a bachelor. i m sexually romantic so i think my life resolves and always has resolved around women. hefner continued to live out the playboy fantasy even in his later years surrounded by busty blond women hosting extravaganza parties with celebrity guests