Demi Moore’s Dating History: A Timeline of Her Marriages and Flings

Demi Moore’s love life has been a topic of discussion over the years, something she chose to approach openly when writing a memoir. In her 2019 book, Inside Out, Moore delves into her past romances, including her marriages to Bruce Willis and Ashton Kutcher. The actress claimed that Willis expressed uncertainty about their marriage after the birth of their eldest daughter, Rumer, in 1988. “But Bruce didn’t want to be the guy who walked out on his family, who did that to his kid,” she wrote. “When he left to do Hudson Hawk, things were in a very precious state. I went over to visit once, and, frankly, I had the feeling that he had screwed around.” Her relationship with Kutcher, on the other hand, felt like a “do-over.” She explained: “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 twenties.” The Margin Call actress suffered a miscarriage during her and Kutcher’s relationship, losing the baby six months into her pregnancy. She had already chosen the name Chaplin Ray. In the memoir, Moore also revealed that threesomes were one of the factors behind the duo’s 2011 split. “I wanted to show him how great and fun I could be,” she wrote, deeming the group sex a “mistake.” She later saw media reports of Kutcher’s affair with a pilates instructor, and she claimed he tried to deflect blame when she asked him about the reports. “Because we had brought a third party into our relationship, Ashton said, that blurred the lines and, to some extent, justified what he’d done,” she wrote. After her romantic ups and downs, Moore began to heal by starting to put herself first. "It's a process of learning to love yourself," the G.I. Jane star explained on an episode of SiriusXM’s The Jess Cagle Show in July 2020. "Accepting who you are just as you are. For me, I had changed myself so many times over and over to fit what I thought somebody else wanted." Moore continued, "It's that idea that we're kinda conditioned to work toward being desired, but we're not supposed to have desires of our own. It really is commendable in our disposal times to go through the journey of really honoring the love that brought you together in the first place and to really give it everything you've got. But you can't do that without that love and acceptance of yourself." Scroll down for a timeline of Moore’s high-profile relationships, including her engagement to Emilio Estevez and her fling with Jon Cryer: