The actor romanced January Jones and Brittany Murphy before his headline-making relationship with the Ghost star. Kutcher and Moore then tied the knot in September 2005 despite their 15-year age difference.
“He was 25,” the actress wrote in her 2019 memoir, Inside Out. “I was 40. But I’m telling you: we couldn’t feel it. We were totally in sync from our very first conversation.”
“Keep in mind, when I was 25, I became a mom,” she explained. “I skipped straight from being a young adult into motherhood and marriage. When I met Ashton, it almost felt like a do-over, like I could just go back in time and experience what it was like to be young with him — much more so than I’d ever been able to experience it when I was actually in my 20s.”
The pair eventually split after reports that Kutcher was unfaithful, and they finalized their divorce in November 2013.
Amid his heartbreak, the Two and a Half Men alum moved on with his former That ‘70s Show costar Kunis. They began a casual relationship in 2012, but sparks soon flew.
“I did a movie called Friends With Benefits. He did a movie that was very similar: No Strings Attached,” the Bad Moms star detailed on the “WTF With Marc Maron” 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.”
Kunis recalled telling Kutcher that she was in love with him, and the next day, he asked her to move in with him. From there, the couple married in July 2015 and welcomed daughter Wyatt and son Dimitri.
Elsewhere in the interview, the Spy Who Dumped Me actress defended her husband’s past marriage to Moore. “They had, like, a normal, real relationship,” she insisted. “They had three kids they were raising. It was, like, a normal life. … Yeah, he was younger, but he loved those kids.”
Scroll through the gallery below to revisit Kutcher’s dating history through the years.