Artists, Heirs, and More Men Who Mary-Kate and Ashley Olsen Have Dated

Ashley began dating Columbia University quarterback Matt Kaplan in 2001. They were together for three years before splitting in 2004. A rep for the New York Minute star released a statement at the time, saying that the breakup was “amicable,” they “parted on good terms,” and “they wish each other the best." Matt is now engaged to The Originals actress Claire Holt.