[post_page_title]Hugh Hefner[/post_page_title]
While Woody Allen gets 100% on the weird factor, Hugh Hefner wins the age gap for sure! The founder of Playboy was 86 years old when he finally married again (he famously had numerous girlfriends, but there was a long gap between his second and third marriages). His new bride, Crystal Harris, was 26 years old when the two tied the in 2012 – that’s a 60-YEAR age gap. They were married until his death in 2017.
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