Ashley Olsen and Jared Leto were first rumored to be an item in 2005 after being seen out on a “cozy date,” according to Us Weekly. At the time, Olsen had just split from her restaurateur-boyfriend Scott Sartiano after the two dated for less than a year. A source told the outlet that Olsen was “like a giddy schoolgirl who has a new man” with Leto (via Hollywood.com). While their romance fizzled out, she and the actor would be seen again together at the Art of Elysium gala in L.A. in 2008. An eyewitness told Us Weekly that the pair “looked like a couple” and “were making out” during the event. However, at that time, an insider close to Olsen denied that the two were back on. “They’re friends,” the source insisted (via Huffpost).
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Following her split from Justin Bartha, Olsen ignited rumors of a rekindled romance with Leto after the two were seen enjoying a “very flirtatious meal” at the Polo Lounge in Beverly Hills in 2012. New York Daily News reported that the pair couldn’t get their hands off each other — with Leto constantly caressing Olsen’s arm and Olsen putting her head on Leto’s lap at one point. But while it seems that they were deeply in love, things ultimately didn’t pan out for the two. Leto would eventually get back together with his ex-girlfriend Scarlett Johansson, while Olsen would move on with businessman David Schulte in 2013.