For Playboy mogul Hugh Hefner, mixing business and pleasure is a way of life. Most of the many relationships he's had over the past six decades have been with ladies who have posed for his iconic magazine. The 86-year-old is back in the headlines for his re-engagement to 26-year-old Playmate Crystal Harris, so let's take a look at some of Hugh Hefner's hottest hook-ups over the years.
