Ashton Kutcher's Entire Dating History

Okay, so I’ll just put it bluntly: before his marriage to Mila Kunis, Ashton Kutcher’s dating history was so chaotic.

Kutcher has been in the public eye for decades, and for years, people had a huge crush on him. (Remember Man Crush Monday? He was always someone’s.) And as the public’s crush for a very long time, many wanted to know about his dating life.

While people know about his marriage to Kunis and, before her, Demi Moore, many don’t know about his other relationships or his alleged flings Besides Kunis, and Moore, Kutcher has dated quite a few other iconic celebrities (like some of his beloved co-stars). Along with that, it’s been a ledge that he’s had flings with multiple A-Listers, including a potential couple of affairs.

As we said, his dating history gets quite complicated. But we have all the details.

Below, check out Kutcher’s entire dating history:

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Mila Kunis (2012-)

Mila Kunis and Kutcher met on the set of That 70s Show when she was 14, and he was 19, but they didn’t start dating until 2012 after reconnecting at an A-list party. They got engaged two years later, in Feb 2014, and married in July 2015. They share two children together named Wyatt, born in Oct 2014, and Dimitri, born in Nov 2016.

Rihanna (2012)

Okay so Rihanna and Ashton Kutcher allegedly had a fling, and they made headlines for it back in 2012. The story goes that they met at a mutual friend’s house in Dec 2011, and she was spotted leaving his house in the AM, per Nicki Swift.

Sarah Leal (2011)

Okay, so one woman came forward to corroborate Demi Moore’s cheating allegations: a woman named Sarah Leal.

She claimed to Us Weekly that Kutcher slept with her at San Diego’s Hard Rock Hotel back in September 2011, specifically on the night of his six-year anniversary with Moore.

Lindsay Lohan (2004 or 2006)

Okay, so people thought Lindsay Lohan and Ashton Kutcher had an affair while filming the 2006 film Bobby. Now, these rumors swirled on even more when he was listed on Lohan’s infamous list of celeb lovers, per DailyMail.

Demi Moore (2003-2011)

Demi Moore and Ashton Kutcher started dating in 2003 after meeting through mutual friends. They married in late 2005 and were together for years before he filed for divorce in Dec 2012. Their divorce was finalized in Nov 2013, amid rumors of his infidelity.

In her memoir, she wrote about his alleged infidelity, including threesomes he pressured her to get into.

Brittany Murphy (2002-2003)

Brittany Murphy and Ashton Kutcher started dating after meeting on the set of Just Married. They only ended up dating for five months, but they apparently wore matching rings at one point, making many believed they were briefly engaged.

Ashley Scott (2001-2002)

Ashton Kutcher and Ashley Scott allegedly dated for a little less than a year in 2001, to 2002.

Ashley Ellerin (2001)

Back in early 2001, Kutcher started seeing a 22-year-old fashion student named Ashley Ellerin. He said that he “was trying to take her on a date” to a Grammys afterparty, but no one answered the door, so he thought he was “too late and she [had already] left.” She was actually murdered that night by Michael Gargiulo, a.k.a. the “Hollywood Ripper.”

January Jones (1998-2001)

Kutcher and January Jones dated from 1998 to 2001, and it was apparently quite toxic. They seemed in love, and moved in together rather quickly, but he was allegedly not supportive of her acting career. While she never confirmed or denied her quote was about him, what she said had people convinced it was about him, per GQ: “The guy I was dating when I first got to L.A. was not supportive. He was like, ‘I don’t think you’re going to be good at this.’ So — f*** you!”

Along with that, Kutcher allegedly accused Jones of cheating on him with her pal Bruce Willis. And per Demi Moore’s memoir, when Jones was asked about it, she said, “Are you serious? I told him [Kutcher] a hundred times, I didn’t want to f*** that old man!”

Monet Mazur (1995-1996)

Kutcher and actress Monet Mazur had a low-key relationship, dating as teenagers from 1995 to 1996, per Us Weekly.