The couple played fictional on-again, off-again lovers Michael Kelso and Jackie Burkhart when the show aired from 1998 to 2006. Instead of letting their romance blossom while working together, the pair waited until 2012 to start dating. In fact, while discussing their relationship on The Howard Stern Show in June 2017, Ashton revealed that Mila felt like his “little sister” when they first started filming the sitcom. “I think I was her first kiss, like, on the show,” he explained. “It was really weird. I was like, ‘Isn’t this illegal?’ It was really awkward. She was 14! … I wanted to make sure she was OK.”
Following the show’s success, both Ashton and Mila went their separate way and entered into long-term relationships with other people. The Ranch actor married Demi Moore in 2005 and finalized their divorce in November 2013 while the Bad Moms actress started dating Macaulay Culkin in 2002. Their split was announced in January 2011. After their respective breakups, Ashton and Mila finally struck up a romance.
“I did a movie called Friends With Benefits. He did a movie that was very similar: No Strings Attached,” the actress explained during an appearance on the “WTF” podcast in July 2018. “We lived our movies out, where we were like, ‘Let’s just hook up. Let’s have fun. We’re both single. We both trust each other. Everything’s great.’ None of us wanted tension. OK, great. We hooked up for three months. And just like our movies, one of us caught feelings.”
As it turned, out, she was the one who got emotionally invested! “I felt like I got punched in the gut, literally overnight,” Mila told podcast host Marc Maron. “He said something, and I was like … ‘Oh, my God. I love this man, and I have to walk away because this is not the agreement that we had. And so I’m going to speak up.’”
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And the rest, as they say, is history! Once she admitted her feelings to Ashton, he asked her to move in with him. The pair got engaged in February 2014, then months later welcomed their first child — a daughter named Wyatt — in October 2014. After they officially tied the knot in July 2015, Ashton and Mila welcomed baby No. 2 — a son named Dimitri — in November 2016. Now they’re one big, happy family.
Scroll through our gallery for a complete timeline of Ashton and Mila’s relationship.
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