Ashley Olsen’s Complete Dating History: Jared Leto, Lance Armstrong and More

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Ashley Olsen's Complete Dating History: Jared Leto, Lance Armstrong and More

All grown up! Years after making it big as a child star, Ashley Olsen has had her fair share of romantic ups and downs. 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. [jwplayer xuiXDMm1-zhNYySv2] 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. [podcast_block]

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Matt Kaplan

The New York Minute star started dating the former Columbia University quarterback in 2001. They were together for three years before their "amicable" split. Kaplan later went on to be engaged to The Originals actress Claire Holt from 2016 to 2017.

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Scott Sartiano

In 2004, Ashley was introduced to the nightclub owner, who she reportedly met through Full House costar John Stamos. The pair's relationship lasted for less than a year.

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Jared Leto

The former child star was first linked to the Thirty Seconds to Mars singer in 2005 after they were spotted on a cozy date together in Los Angeles. Three years later, an eyewitness told Us that they "looked like a couple" when they were caught kissing and holding hands at the Art of Elysium gala. The duo reunited once more for a romantic Beverly Hills evening in 2011.

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Greg Chait

Following her split from Sartriano, Ashley moved on with Tsubi Jeans CEO Greg Chait. Page Six reported that the pair's flame fizzled out in 2007, citing "commitment issues" as the reason they parted ways.

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Lance Armstrong

Ashley sparked up a brief romance with the infamous cyclist in 2007 shortly after Armstrong's split from Tory Burch. Years later, a tell-all book written by the New York Times' Juliet Macur alleged that Armstrong was "warned" not to involve himself with the then-21-year-old actress. 

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Justin Bartha

Though she tended to keep her love life relatively private, the Passport to Paris star's three-year relationship with the Hangover actor was her most public to date. After the duo called it quits in 2011, Bartha went on to marry fitness expert Lia Smith, with whom he shares two daughters.

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David Schulte

Us confirmed in September 2013 that Ashley was dating the Oliver Peoples CEO, but multiple sources confirmed their split less than five months later. "He was a great guy and cute, but it didn't work out," an insider said at the time. Despite their breakup, Schulte was named president of the Olsen twins' fashion brand, The Row, in 2016.

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Bennett Miller

Ashley was spotted getting cozy with the Foxcatcher director while he was working on the 2014 sports drama with Steve Carell and Sienna Miller. Two years later, Us confirmed that the Moneyball director and Sienna were a couple.

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George Condo

The Full House alum was briefly linked to the New York City-based artist one year after his separation from his wife of 26 years, Anna Condo, in 2015.

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Richard Sachs

Ashley took her relationship with the financier public in October 2016 while on a double date with Mary-Kate and her now-estranged husband at a basketball in NYC. Us confirmed that the duo parted ways five months later because Ashley wanted to "focus on her clothing line."

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Louis Eisner

The It Takes Two actress began quietly dating Eisner in 2017 after years of friendship. Though the couple have kept their relationship under wraps, they sparked engagement rumors in July 2019 when Ashley was seen sporting a ring on her left hand on a romantic L.A. date night. The pair made their red carpet debut in September 2021 at the YES 20th Anniversary Celebration, which marked Ashley’s first red carpet appearance in nearly two years.

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Dax Shepard

The Parenthood alum revealed during a February 2022 episode of his "Armchair Expert" podcast that he and Ashley dated more than a decade prior. "I dated Ashley Olsen. And she’s just the most wonderful person. She's fantastic," Shepard said, adding that the pair were together when Ashley was launching The Row with her sister. "When we were dating, it was when she was putting all her energy and focus into launching that in a big way. So, I was able to see her meet with design teams and, like, run her s--t and she handled her [business], and it’s very impressive," he said, describing Ashley as being "super funny, and sarcastic and intelligent."