5. Hugh Hefner & Crystal Harris
This one is a no-brainer, but we definitely couldn’t leave the king of open marriages off of this list! Hugh Hefner has lived the life most bachelors dream of, and he has famously flaunted his polyamorous relationships on a reality show. His ex-girlfriend, Holly Madison, even wrote a book in which she detailed her group sex sessions with Hef, his other girlfriends, and various random women. Hef has since married Crystal Harris, and although the two have kept quiet about their relationship, we’re pretty certain the 89-year-old eternal playboy hasn’t changed his ways when it comes to inviting other women into his bedroom.
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