Hugh Hefner's Playmate Girlfriends

Newlywed Hugh Hefner turns 87 today! Bachelor no more, he tied the knot on New Year's Eve with his 60-years-younger fiancée, Crystal Harris, whom he's dated for nearly four years. The pair called off their 2011 nuptials just days before the big day, but after reuniting in 2011, Crystal is officially Hugh's wife No. 3 — third time's a charm? Crystal isn't the first young Playboy Playmate Hef has been romantically linked to, and I'm sure she won't be the last. Since his divorce from first wife Mildred Williams in 1959, the magazine mogul has been with many well-endowed lady friends, sometimes two or more at a time! See some of the Playmates Hef has been paired up with over the past five decades.