From Cameron Diaz to Katy Perry –– Take a Look at Jared Leto's Dating History

From acting to music, Jared Leto has spread his wings in the entertainment industry for decades now. The WeCrashed actor and 30 Seconds to Mars musician — who got his big break on MTV's angsty '90s drama My So-Called Life — took home an Oscar in 2014 for Dallas Buyers Club, and his career hasn't showed any signs of slowing down.

Over the years, Jared has been involved in a handful of relationships with some of Hollywood’s most gorgeous and popular starlets. Here’s a breakdown of some of his past reported relationships — including who he's currently said to be dating.

From 1999 to 2003, Jared was involved with Cameron Diaz. Her major blockbuster flick There’s Something About Mary hit theaters and everyone was totally obsessed with her at the time … including Jared, clearly. When Cameron and Jared were dating, they were obviously taking things super seriously because they reportedly ended up getting engaged! Sadly, they quietly parted ways in 2003 without publicizing the reason.

Jared‘s first go at a relationship with Scarlett Johansson reportedly took place in 2004. Because of their 13-year age gap, fans didn’t really have too much hope that they’d survive as a couple. Fast forward to 2012, and Scarlet and Jared briefly reconnected. Although they were spotted holding hands and getting close once again, it didn’t last for long.

Around the same time Jared and his band 30 Seconds to Mars were picking up steam in 2005, he reportedly started dating Ashley Olsen. As his band was just starting to take off, she was doing her best to ease out of the public eye after a childhood career as an actress. They reconnected in 2008, and then tried again for the third time in 2011. No matter how many times Ashley and Jared attempted to get back together, it simply wasn’t meant to be.

Just like Jared‘s relationship with Ashley, his relationship with Lindsay Lohan continually remained hot and cold starting in 2006. Jared and Lindsay filmed a movie called Chapter 27 together and were said to have hit it off on set. Their relationship never remained consistent or solid, though. In 2014, when Kode magazine allegedly asked her if Jared was good in bed, she reportedly confirmed, "Oh yeah!"

It seemed that Jared and Paris Hilton made a great match when they were spotted getting close and personal at the 2008 Sundance Film Festival. Since both celebrities were considered super flirtatious at the time, their short-term thing wasn’t exactly shocking to anyone.

When Jared was continually spotted hanging out with two beautiful European supermodels in 2011, fans were quick to jump to the assumption that he was potentially entertaining two separate women at the same time. One of those women was Nina Senicar and the other was Katharina Damm.

Starting in 2013, and picking back up in 2018, Chloe Bartoli was reportedly involved with Jared on a “friends with benefits" level. You might recognize Chloe's name from Keeping Up With the Kardashians since she was also previously romantically connected to Scott Disick.

Lupita Nyong’o and Jared sparked dating rumors in 2014. There was a lot of obvious chemistry between them, and at one point, she said that what they shared was something “that goes beyond the dating rumors, beyond all that," according to Porter. What exactly did they share? We may never know.

Around the same time that Jared and Lupita were rumored to be secretly dating, conversations about him and Miley Cyrus also began making their rounds. Keep in mind that Miley's around two decades younger than Jared! It turns out they had a lot of shared interests including their appreciation for art, nudity, and music.

2014 was obviously a big year for Jared since he was connected to both Lupita and Miley that year. Interestingly enough, he was also spotted going on a date to Coachella with Katy Perry! This was around the same time she ended her relationship with John Mayer, and she hadn’t started dating Orlando Bloom just yet.

Jared‘s relationship with Russian model Valery Kaufman has reportedly been in the works off and on since 2015. Jared and Valery have a massive age gap of 23 years, but that obviously hasn’t stopped them from trying to make things work over the years. She also appears to be the most recent woman involved in his life.