Popsugar Celebrity Celebrity Couples Who Have the Olsen Twins Dated? Artists, Heirs, and More Men Who Mary-Kate and Ashley Olsen Have Dated June 25, 2018 by Britt Stephens View On One Page Photo 13 of 22 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 13 Max Winkler Mary-Kate dated Henry Winkler's son Max for a few months in 2002. Previous Next Start Slideshow Ashley OlsenMary-Kate OlsenCelebrity CouplesCelebrity FactsCelebrity Breakups