1. Hugh Hefner & Crystal Harris
Legendary Playboy Hugh Hefner has been slaying the ladies for decades and released the first ever issue of Playboy magazine in 1953 with cover model Marilyn Monroe. The world famous ladies’ man has been married three times (so far) in his 90 plus years.
Most recently he got hitched to model Crystal Harris who is 60 years younger than him. He and Harris started dating in 2008, were engaged in 2011, and have been married to each other since 2012, holding the ceremony at the infamous Playboy Mansion.
Hefner has four children (all from previous relationships) with his youngest child born in 1991, and five years younger than Step-Mother Crystal.
Sources: EOnline, Therichest, OK Magazine, DailyMail.co.uk, ETOnline, HuffingtonPost
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