Ashley Olsen: A Look Back at Her Complete Dating History

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 considering popping the question.

Olsen began dating Still House Group artist Louis Eisner in 2017, sparking engagement rumors two years later. The duo reportedly wed in secret in December 2022, with Us confirming in August 2023 that they had welcomed their first child together: a baby boy. 

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