Just five days before their nuptials, Hugh Hefner’s fiance, Crystal Harris, called off their engagement. The reason for the split is reportedly because the 25-year-old Harris wanted to pursue a music career rather than settle down with the aging playboy. Harris was set to be Hefner’s third wife, and Hef decided to opt out of a prenuptial agreement this time around because he “actually cares” about his blonde now former fiance.
Although Hef might be heartbroken, there are plenty of aspiring bunnies dying to fill Harris’ coveted “#1 Girlfriend” spot. Throughout his time in the spotlight, the now 85-year-old Hef has proved that he’s a professional ladies man and surely won’t have much difficulty finding new arm candy.
In honor of Hef and Crystal’s romance, we’ve rounded up shots of the 12 bunnies that stole the eternal playboy’s heart. And while we’re sure Hugh’s had a few more girlfriends, here are the most memorable women he’s wooed over the years.