The actress-turned-fashion mogul tends to keep her love life on the down low, but has been involved with a number of high-profile men throughout the years. In 2001, Olsen sparked up a serious romance with former Columbia University football star Matt Kaplan, who went on to become a successful film producer and CEO of Ace Entertainment.

Shortly after Olsen and Kaplan’s flame burned out in 2004, the Two of a Kind alum had a series of flings with Scott Sartiano, Jared Leto, Lance Armstrong and Greg Chait. It wasn’t until 2007 that the Influence author landed in another long-term relationship, this time with actor Justin Bartha. The former pair were so serious that an insider told Us Weekly in 2010 that the National Treasure star was considered popping the question.

“He’s in love and is just waiting for the right time,” the source said at the time. Five months later, however, Us confirmed that the couple had called it quits.

More recently, Olsen has been linked to Still House Group artist Louis Eisner. The pair have been quietly dating since 2017 and sparked engagement rumors two years later while on a romantic night out in California — with Olsen noticeably sporting a ring on her left hand.

The pair made their red carpet debut in September 2021 at the YES 20th Anniversary Celebration, which supported the Young Eisner Scholar foundation run by his dad, Eric Eisner. The New York Minute star stepped out in an all-black ensemble and tied her hair in a sleek bun. Louis, for his part, sported a fitted black suit and a white button-down underneath.

The pair’s rare red carpet appearance marks their second public outing in months, after the Columbia University alum shared a now-viral pic of Ashley in July 2021 during a hike, where she held a drink and a machete in each hand.

Despite her rocky romantic life, Ashley has always had her twin sister, Mary-Kate Olsen, by her side. In May 2020, Us confirmed that Mary-Kate signed a petition for divorce from Olivier Sarkozy one month earlier and was seeking an emergency order to end her marriage due to court closings amid the coronavirus pandemic. The duo tied the knot in November 2015.

While their separation may be off to a messy start amid the global health crisis, an insider told Us that Mary-Kate has an “iron-clad prenup” and that “her business interests and fortune are protected.” Shortly after news broke of their split, TMZ reported that Mary-Kate hopes the prenup agreement will be strongly enforced.

Scroll down to learn more about Ashley’s notoriously private dating life.

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This story originally appeared on: US Magazine - Author:Meredith Nardino