Charlize Theron, 44 And Sean Penn, 59—15 year difference

They dated for about a year and a half before they split, and rumor has it that their split was less than amicable. There’s really no clue as to what made them go their separate ways, and all we’ve heard from Theron’s side is that the relationship simply “didn’t work anymore.” Whatever the case may be, what’s interesting about their relationship is that they were actually friends for 18 years before they started dating.

It seemed that Theron didn’t have that much wonderful memories towards this relationship. Recently, when she was promoting her new film, she said she was eager to date for she stayed single for 10 years. It was clear that she totally ignored the serious relationship between Sean Penn and her. Well, to some degree, we don’t really expect any relationship that involved Sean Penn to last, given the historical evidence.