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19 Celebrity Couples That Have Huge Age Differences

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12. Bennett Miller And Ashley Olsen: 20 Years

12. Bennett Miller And Ashley Olsen: 20 Years

shley Olsen began dating Bennett Miller in 2014, when he was 47 and she was 27. Since then, she has also been linked to 58-year-old Manhattan artist George Condo, who was reportedly married during his relationship with the Olsen twin. It seems this Olsen has a thing for older men, but we aren’t judging.

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