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Ex-Loves Of Her Life! See All Of Ashley Olsen's Former Flames Throughout The Years: Photos

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Source: mega

Jun. 4 2022, Published 12:01 a.m. ET

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Ashley Olsen has done her fair share of dating!

While the trend setter typically keeps her love life private, many of her exes have been some of Hollywood's hunkiest men!

Scroll through the gallery to see all of Ashley Olsen's former flames.

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Matt Kaplan

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Source: Extra Butter: Celebrity Interviews & Movie Reviews/youtube

One of Ashley's first big romances was with Matt Kaplan, the Columbia University quarterback in 2001. The young duo dated for nearly three years before going their separate ways.

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Jared Leto

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Source: mega

In 2005, the Two Of A Kind star was spotted with Jared Leto when they were seen out together in Los Angeles. Three years later, an eyewitness told Us Weekly that the duo “looked like a couple” when they were caught kissing and holding hands at the Art of Elysium gala.

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Lance Armstrong

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Ashley and Lance Armstrong dated while the actress was 21 and the cyclist was 36 back in 2007. The short-lived couple was spotted getting close at the Rose Bar inside the Gramercy Park Hotel, and on a few other dates around New York City.

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Justin Bartha

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Source: mega

One of the fashion designer's most public relationships was with actor Justin Bartha. The couple dated for two years before splitting in 2011. Although Ashley is typically private with her romances, she and The New Normal star walked many red carpets as a couple together.

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Dax Shepard

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During an episode of his hit podcast Armchair Expert, Dax Shepherd revealed he dated Ashley “15 or 16 years ago”. While the former couple stayed under the radar, the actor had nothing but praise for his former flame, “She's just the most wonderful person. She's fantastic."

Around the time they were dating, Ashley was launching The Row. "When we were dating was when she was putting all her energy and focus into launching that that in a big way. So I actually got to see her, like, meet with design teams and, like, run her s--t," he said.

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Richard Sachs

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Source: mega

In 2016, the mogul was spotted with art collector and much older man, Richard Sachs, who was 28-years her senior. The two dating for five months, often being photographed getting cozy at New York Knicks vs. Brooklyn Nets games and hanging out with Ashley's twin sister.

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