News Ashley Olsen's Boyfriend Is Even Older Than Mary-Kate's By Antoinette Bueno 12:17 PM PDT, August 4, 2014 FameFlynet Ashley Olsen, 28, was spotted out with her boyfriend director Bennett Miller in New York City on Sunday, who at 47 years old, is 19 years her senior. Miller, the director of such critically acclaimed hits as Moneyball, Capote and the highly anticipated Foxcatcher, started dating Olsen earlier this year. Video: The Olsen Twins Play an Awkward Game of 'Her or Me' The two went public when she stepped out with him at Philip Seymour Hoffman's funeral in February -- Miller was close friends with the late actor, directing him in Capote. On Sunday, the couple was snapped leaving her New York City apartment, Olsen going makeup-free and Miller looking casual in jeans and a t-shirt. Related: Mary-Kate Olsen Engaged to Olivier Sarkozy And while everything appears to be going strong between Ashley and her man, the same can be said for her sister Mary-Kate -- she's engaged to French businessman Olivier Sarkozy, 45.