Is Ashley Olsen’s May-December Relationship with This 47-Year-Old Hollywood Director Just a Rebound?

Ashley Olsen’s May-December Relationship Hollywood Director Bennett MillerThey say twins are alike in almost every way; that’s def­i­nitely true for the 27-year-old Olsen sis­ters. Mary Kate Olsen has been dat­ing a much older man, 44-year-old banker Olivier Sarkozy, since May 2012, and her twin sis­ter, Ash­ley, also has a thing for dat­ing men who are almost twice her age.

Back in Jan­u­ary, Ash­ley Olsen ended her five-month May-December rela­tion­ship with 44-year-old mil­lion­aire busi­ness­man David Schulte. “He was a great guy and cute, but it didn’t work out,” an insider told Us Weekly. Less than a month later, Ash­ley has found her­self a new older man—she’s report­edly dat­ing 47-year-old Mon­ey­ball direc­tor Ben­nett Miller.

The new celebrity cou­ple has been spend­ing a lot of time together in L.A., where Ben­nett Miller has been work­ing on his next movie, and Ash­ley Olsen even sup­ported her new older man at the funeral of his close child­hood friend, actor Philip Sey­mour Hoff­man. Hope­fully this May-December rela­tion­ship will be a lit­tle more suc­cess­ful than her last one.

What do you think: Would you date an older man who was twice your age?


Larkin, M., “It’s over! Ash­ley Olsen splits from mul­ti­mil­lion­aire busi­ness­man David Schulte after less than six months of dat­ing,” Daily Mail web site, Jan­u­ary 15, 2014;

McRady, R., “Exclu­sive: Ashely Olsen Is Dat­ing Mon­ey­ball Direc­tor Ben­nett Miller,” Us Weekly web site, Feb­ru­ary 13, 2014;

Photo Credit: Helga Esteb / (Ben­nett Miller), Everett Col­lec­tion / (Ash­ley Olsen)