Matt Kaplan dated Ashely Olsen from 2001 until 2004. Although they obviously weren’t meant to be in each other’s lives forever, Ashely was enthused about the relationship for a time. During a Rolling Stone interview, 17-year-old Ashley shared a few factoids about her bond with then-college freshman Kaplan. “We go out to dinner, go to a movie,” shared Ashely with the outlet. “It’s pretty boring.” Ashley also revealed that her sister, Mary-Kate Olsen, sometimes third-wheeled on their dates. “At the very beginning, I would probably not have my sister come along,” said Ashley. “It takes time to get to where you’re comfortable having a third wheel around. But then we’ll all go out to dinner and have so much fun,” she added.
Read Related Also: Emergency outside Dan Andrew's office in Melbourne, in Noble park
Unfortunately, the couple broke things off in May 2004, according to People, who reported that the breakup was “amicable.” Prior to their break up, the New York Post inferred that Kaplan, who was attending Columbia University at the time, at least partially influenced Ashley’s decision to attend NYU. In September of that year, the New York Post reported that Kaplan and Mary-Kate’s ex, David Katzenberg played wing-men to each other and flirted with multiple women at a Maxim Music party. Well, that’s one way to cope with a breakup.
