Ashley Olsen's Loves & Hookups

Who is Ashley Olsen dating? Who Ashley Olsen dated; list of Ashley Olsen loves, ex boyfriends; breakup rumors.. The loves, exes and relationships of Ashley Olsen, listed by most recent. Olsen twins fans will also enjoy hot Ashley Olsen pics and Mary-Kate Olsen's dating history. The twin has kept a surprisingly clean record, but then again, who has time to date when you're running a multi-billion dollar empire? Wonder if somewhere amongst all those teen videos is a decidedly adult celeb "tape?" There's never been any celebrity tapes with twins, so that would be a real shock to the celebrity tape game. For now, the tiniest Tanner has yet to appear on the list of celebrities with such tapes but she's got time...

This list contains Ashley Olsen's famous exes like Jared Leto, Bennett Miller, and Justin Bartha.

  • Louis Eisner

    Ashley Olsen sparked engagement rumors after she was spotted wearing a ring on that finger while out with boyfriend Louis Eisner in Pacific Palisades in July 2019. 

    Olsen has been dating artist Eisner for almost two years. The pair were seen double dating with her twin sister Mary-Kate Olsen and her husband Oliver Sarkozy in June. 

  • Richard Sachs
    Photo: Wikimedia Commons / CC-BY

    Richard Sachs

    In March 2017 Ashley Olsen and financier Richard Sachs split after five months of dating.

    The pair began dating in late 2016. There was a 28-year age difference. 

    • Age: 58
  • Bennett Miller
    Photo: flickr / CC0

    Ashley Olsen started dating director Bennett Miller since 2014. The pair broke up about a year later.

    Bennett Miller (born December 30, 1966) is an American film director, known for directing the acclaimed films Capote (2005), Moneyball (2011), and Foxcatcher (2014). He has been nominated twice for the Academy Award for Best Director.
    • Age: 56
    • Birthplace: New York City, New York
  • David Schulte
    Photo: david_shankbone / flickr / CC-BY 2.0

    David Schulte

    Ashley Olsen reportedly dated David Schulte from 2013 - 2014.

  • Johnny Depp
    Photo: modenadude / flickr / CC-BY-NC-ND 2.0

    In 2012, Ashley Olsen was rumored to be dating Johnny Depp after he was seen leaving her NYC apartment.

  • Justin Bartha
    Photo: Justin Bartha / Wikimedia Commons
    Ashley Olsen and Justin Bartha were in a relationship from 2008 - 2011.
    Justin Lee Bartha (born July 21, 1978) is an American actor, known for his roles as Riley Poole in the National Treasure film series, Doug Billings in The Hangover trilogy, and David Sawyer in the NBC comedy series The New Normal. He starred as Colin Morrello in the CBS All Access legal and political drama The Good Fight.
    • Age: 44
    • Birthplace: Fort Lauderdale, Florida, USA