Ashley is famous for her colorful dating history, and a penchant for dating men much older than her age.
Ashley Olsen's dating history can be traced back to 2001 when she was linked with actor Matt Kaplan, who is the only boyfriend gossiped to be dating Ashley; resembling her age. After dating for three years, Ashley and her boyfriend parted in amicable terms in 2004.
After the actor, she was linked with nightclub owner Scott Sartiano, actors and entrepreneur Greg Chait in the time interval of 2005 to 2008. The striking similarity with all three was they were all much older than Ashley.
Her long line of rumored boyfriends also included Lance Armstrong, Justin Bartha, and David Schulte from 2008 to 2014. She was again linked with director Bennet Miller, who was 19 years her senior in 2014. After being connected with George Condo, a whopping 29 years older than her, Ashley seemed to have settled with art dealer Richard Sachs.
The duo was seen displaying PDA at a basketball game in November 2016 which confirmed rumors about their relationship. Richard and Ashley, who had an age difference of 27 years, looked every bit in love and it seemed that he was the man Ashley would finally turn her husband.
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What's more, her sister, who also has a long history of dating old dudes, married banker Olivier Sarkozy in 2015, leading calls for Ashley to get married and settle down. However, Ashley's relationship with the art dealer too did not last long, and the boyfriend-girlfriend duo split in March 2017, citing that she wanted to focus more on her career.
After the high profile breakup, news about Ashley's boyfriend has not made the limelight. This time she could be focusing on her career, and after numerous failed relationships, her wanting to be single is understandable.
