If you didn't know better, Hugh Hefner would just be your average geriatric in a nightclub, wearing a captain's hat and falling asleep surrounded by 30 beautiful women. But he isn't. He's Hugh effing Hefner, people, and he's unsurprisingly taken so many women back to Gollum's lair his bedroom that he's lost track.
Not content with all the tail he was regularly getting in the Playboy Mansion and eager for something deep and real, Hugh Hefner finally tied the knot with generic bimbo Crystal Harris, who was likely eager for bank accounts that were also deep and real.
Hugh Hefner has been in the "game" for a long time, but over the past few years it seems like he is being dumped a lot. The most recent, being dumped by fiancee Crystal Harris, had to hurt the worst.