Inside Demi Moore And Ashton Kutcher's Relationship

This feature discusses addiction, drug misuse, and miscarriage.

Before Demi Moore and Ashton Kutcher's ill-fated love story began playing out in the tabloids, both actors had relationships with big stars. Moore was married to "Lethal Weapon" actor Bruce Willis from 1987 to 2000, so she was with him when she landed some of her biggest roles, including "Ghost," "Indecent Proposal," and "A Few Good Men." She also received $12.5 million for the 1996 movie "Striptease," which was the largest salary a female actor had been paid at the time.

When Kutcher entered Demi's life in 2003, it would still be a decade before the "That '70s Show" star became Forbes' top earner on TV with his estimated $24 million salary for a year's work on "Two and a Half Men." Prior to Demi, he dated the late "Clueless" star Brittany Murphy and "Mad Men" actor January Jones, whom Demi spilled some piping-hot tea about in her memoir "Inside Out" (via Radar). When they were engaged to be married, Kutcher purportedly believed that Jones cheated on him with her "Bandits" co-star, who was none other than Willis. According to Demi, she once asked Jones if she did, indeed, have a fling with her ex-husband. She recalled Jones responding, "I told [Kutcher] a hundred times, I didn't want to f*** that old man!"

Demi had a broken engagement of her own to her "St. Elmo's Fire" co-star Emilio Estevez, as well as a failed first marriage to rocker Freddy Moore. But we're taking you inside her compelling relationship with Kutcher.

In 2003, Drew Barrymore complained to the Calgary Sun (via Entertainment Weekly) that Ashton Kutcher's romance with her co-star Demi Moore possibly prevented "Charlie's Angels: Full Throttle" from taking flight at the box office. After all, the couple was sucking up a lot of valuable headline space. Barrymore can thank "90210" star Sara Foster, a long-time friend of Kutcher's, for introducing him to Moore. But apparently, Foster's matchmaking magic didn't initially work. In an April 2010 appearance on "Live with Regis and Kelly" (via the Daily Mail) Moore recalled, "The first night I met [Kutcher] he didn't have two words to say to me — he had a singular focus and it was on somebody else."

Moore told Harper's Bazaar that she later captured Kutcher's attention by wearing a slinky blue dress to a play they both attended. "It was an effective evening," she said. There were immediate sparks, but Moore and Kutcher got to know one another better via text message before their romance fully blossomed into the real deal. By the time they decided to brave the paparazzi together, it seems that they had built a pretty solid foundation for a long-term relationship. In 2006, Kutcher told Parade (via CBS News) that he and Moore were at ease with each other from their first date onward. "We had one argument in the first three months of dating, and since then we haven't had any," he boasted.

From 2003 to 2012, Ashton Kutcher played elaborate pranks on the likes of Justin Timberlake, Halle Berry, and Salma Hayek while hosting "Punk'd." Although the popular MTV reality series was one of Hollywood's hottest tickets at the time, he didn't dare punk Demi Moore. Kutcher explained to TeenHollywood.com (via UPI) that he didn't want Moore to have to wonder whether or not he was pulling her leg if he ever had to inform her that one of her daughters had an emergency. "I can't have been the boy who cried wolf," he said.

While the prolific prankster assured his girlfriend that he would never humiliate her for the sake of entertainment, Moore possibly wondered if there were cameras hidden somewhere when he popped the question. According to him, Kutcher did actually hope to capture the moment on camera, but he joked that he only wanted evidence of Moore saying "Yes" to him. "Just as I was going to propose, I realized I had run out of film," Kutcher recalled, per Young Hollywood. "So I stumbled round all day with this ring burning a hole in my pocket. She kept asking, 'What's wrong, sweetie?' and I couldn't tell her." 

Kutcher decided to try again the following day — which just happened to be April Fools' Day. He worried that Moore would think that he was trying to fool her, but apparently, he managed to convince her that the ring was the real thing.

After their divorce, Demi Moore and Bruce Willis decided to remain a major presence in each other's lives for the sake of their three daughters: Rumer, Scout, and Tallulah. Willis even scored an invite to his ex's wedding when she and Ashton Kutcher got hitched in 2005. The couple had embraced the celeb spiritual craze du jour, so they were married by Moore's Kabbalah instructor, Rabbi Eitan Yardeni who officiated an intimate ceremony at their Beverly Hills residence, per People.

Willis and Moore's amicable uncoupling allowed them to spend the holidays together with their kids, and the exes even started vacationing together with their significant others. "We've become like a tribe," Willis told W magazine in 2009. "... We're really lucky that it turns out we all have fun together. I still love [Moore], and I have a lot of respect for how she lives her life." When Willis married Emma Heming, she became a part of the tribe — and Kutcher and Moore were present at the couple's wedding to help them celebrate. Speaking to Parade (via CBS News) in 2006, Kutcher said of his relationship with Willis, "He's not 'the other guy.' He's not in competition. We have our own friendship."

As for Moore, she told Harper's Bazaar, "I didn't get married and have children so I could get a divorce, get remarried, and get along with my ex-husband. But since that is what happened, I am grateful it turned out this way."

In addition to striking up a friendship with his wife's ex-husband, Ashton Kutcher also worked with him. Bruce Willis appeared alongside Kutcher in a 2005 episode of "That '70s Show," making a cameo as a sleazeball character named Vic. Willis' costume almost made him unrecognizable; it included glasses, a mustache, and a bad brunette wig with bushy sideburns. Vic interviewed Kutcher's character, Kelso, for a job working as a security guard at Chicago's Playboy Club. During their scene, the guys ate some spicy food together and had a few laughs.

When Kutcher replaced Charlie Sheen in "Two and a Half Men," his new co-star, Jon Cryer, didn't know whether Kutcher was aware that he had briefly dated Moore in the '80s. On "Watch What Happens Live," Cryer revealed that Kutcher made him sweat about it during their entire first meeting before finally putting him out of his misery and telling him that Moore had already informed him about their romantic history. "It was a little awkward, I have to say," Cryer confessed.

Another of Moore's exes, her former fiancé Emilio Estevez (who also happens to be Sheen's brother), cast both her and Kutcher in his 2006 historical drama about the assassination of Robert F. Kennedy, "Bobby." Estevez directed the film, while Moore and her husband played a troubled lounge singer and a drug dealer, respectively. When The Washington Post quizzed Estevez about the couple's casting, he called it "divine intervention."

Much ado was made about Demi Moore being 15 years older than Ashton Kutcher. However, as Moore pointed out to ABC News, the next woman her ex-husband Bruce Willis wed was 23 years younger than him. "It's so silly," Moore said of the attention the age gap received. She and Kutcher even poked fun at it during his "Saturday Night Live" monologue in 2005. Moore was only 43 but dressed up like a little old lady, complete with a walker. "My support hose are cutting off my circulation," she complained to Kutcher as he helped her onto the stage. And after the pair shared a passionate kiss, Kutcher pulled away with dentures dangling from his mouth.

Moore was often described as a "cougar" but told Harper's Bazaar that, if people insisted on likening her to a predatory big cat, she'd rather they use the word "puma." She explained, "It has a sweeter quality, more elegant."

Moore and Kutcher insisted that the age thing was never a big deal to them. But in her memoir, Moore does mention age when describing her frame of mind at the time Kutcher entered her life. "I just felt like a 15-year-old girl hoping somebody liked me," she wrote (via ABC News). And according to The Orange County Register, Kutcher was hoping to capitalize on their age difference by producing a sitcom about a man who marries a woman with a daughter who is almost the same age as him.

Time deemed Ashton Kutcher and Demi Moore the "first Twitter celeb couple" because of how active they were on the social media platform during its early years. While Kutcher might not be one of the most prominent Twitter users today, he was the first to reach the million-follower mark. The site's jargon still needed some tweaking when he convinced Moore to join him there. In a 2009 W magazine interview, Moore was speaking about her declaration that she wanted to be known as a "puma" when she said that she "Twittered it out."

As for Kutcher, he argued that Twittering out terms of endearment was a new, modern form of romantic gesture. "In some ways, it's no different than sending flowers to the office: You are declaring your love for everyone to see. Who doesn't like to be publicly adored?" he wrote in a 2010 essay for Harper's Bazaar. 

And he certainly practiced what he preached. "Heading for bed. missing u pillow partner," read a 2009 tweet from Kutcher to Moore. Their short-form public love notes could also be on the steamy side. "Watching my wife steam my suit while wearing a bikini. I love God!" he wrote while the couple was in Turks and Caicos for Bruce Willis' wedding. Not to be outdone, Moore once tweeted, "Grabbing my hubby and putting on my birthday suit ... to snuggle ... goooood night. Until tomorrow!" We also learned from her tweeting that she and Kutcher were big "Jersey Shore" fans.

In a 2009 HuffPost essay, Ashton Kutcher recounts how he and Demi Moore decided that they wanted to find a humanitarian cause to promote and support together. "We were continually confronted with one issue that pulled at our heartstrings and haunted our thoughts: the abolition of 21st-century slavery," he wrote. As they learned more about the issue, they became particularly horrified by the child sex trafficking trade. To raise awareness of the practice, they founded The Demi & Ashton (DNA) Foundation. Kutcher told Reuters that the organization was their Valentine's Day gift to each other in 2010, and as one of their first altruistic acts, they sent flowers to victims of human trafficking.

"It just seemed impossible to live in a world where that was going on and not, you know, do something about it," Moore said during a 2011 appearance on "Piers Morgan Live." According to Kutcher, Twitter served as the perfect platform for promoting their cause because many traffickers use the internet to operate. "So if we can motivate people while they are online to do something about that, then we can make a dent," he said.

Even after the couple split, their foundation's fight to end human trafficking continued. Its name was later changed to Thorn, and in 2017, Kutcher testified before a U.S. Senate committee about how the organization had created software that had been used to find thousands of trafficking victims via the internet, per KTLA5.

Demi Kutcher and Ashton Kutcher were one of those celeb couples who shared TMI about their relationship on the reg, and this fed into the public's fascination with the pair. "Look, I can't help talking about my marriage and my love because it's all tied together," Kutcher explained to Parade (via CBS News). "My life is intrinsically based on my relationship." One detail he shared with Redbook was that he and Moore didn't jump into bed together right away. "Well, there wasn't anything physical happening for a while," he said (via Us Weekly). 

In a 2005 interview with Harper's Bazaar (via CBS News), Moore revealed that some of her and Kutcher's favorite pastimes involved a lack of clothing, such as watching Court TV and hopping in the tub together. "Snuggling up naked" was something else they did that she wanted the world to know about.

On "Piers Morgan Live," Moore also revealed that Kutcher was quite the romantic, saying that he would write short love notes on Post-Its and leave them all over the house (like a primitive version of tweeting). "Some have been there, I don't know, seven years?" she said. In response to her revelation, Kutcher quipped, "Post-It notes are much cheaper than diamond rings." Moore noted on the show that she and Kutcher had been accused of getting married for publicity, but their willingness to be so open about their relationship helped silence the skeptics.  

In her 2019 ABC News interview with Diane Sawyer, Demi Moore speculated that the media's obsession with her age was tied to her ticking biological clock, something she had felt acutely after she suffered a miscarriage at age 42 and started IVF treatments. She'd already chosen a name for the baby girl that she lost when she was six months pregnant: Chaplin. "I tried to allow myself to mourn, but it was so confusing. How could I grieve a person who'd never been in the world?" Moore wrote in "Inside Out" (via Insider). 

She also revealed that she felt like Ashton Kutcher couldn't fathom the feelings she was experiencing at the time, noting that his own grief didn't include the added layer of being older and fearing that the window of opportunity to have a child was rapidly closing. Of how he felt about the miscarriage, Kutcher told Esquire, "Losing a kid that you think you're going to have, and that close to thinking you're going to have a kid, is really, really painful."

On top of everything else, Moore's loss was exacerbated by the guilt that she'd started drinking again and began to blame herself for the miscarriage. When she reflected back on the miscarriage and her subsequent unsuccessful efforts to get pregnant, she told Sawyer, "I really lost sight of everything that was right in front of me, which is the family I had."

In 2011, Demi Moore and Ashton Kutcher announced that they were divorcing after six years of marriage. In a statement published by People, Moore said, "As a woman, a mother, and a wife there are certain values and vows that I hold sacred, and it is in this spirit that I have chosen to move forward with my life." The announcement came after Us Weekly spoke to a woman named Sara Leal who claimed that Kutcher had unprotected sex with her on his six-year wedding anniversary. Actor Scott Eastwood later claimed that he'd been dating Leal at the time. "It was, I think, the catalyst that broke [Kutcher] and Demi up," Eastwood said on "Watch What Happens Live."

In "Inside Out"  (via Radar), Moore claimed that Kutcher cheated on her twice. She alleged that the other time happened in 2010 with a woman Kutcher met during an outing with Moore's oldest daughter, Rumer Willis. Kutcher purportedly confessed to being unfaithful and tried to defend his behavior by bringing up past threesomes Moore had agreed to (and later regretted). "Because we had brought in a third party into our relationship, Ashton said, that blurred the lines," she wrote (via People).

As for Kutcher, he later told Esquire of the situation, "You own the s*** you did wrong, and you go forward." On "The Howard Stern Show," he'd previously joked about his sex scenes with Katherine Heigl in "Killers" being "like free cheating."

On the fateful night their romance began, Ashton Kutcher overheard Demi Moore calling her daughters to tell them goodnight. "He looked right at me and he said, 'That is the most beautiful thing I ever heard,'" she told The Guardian. Soon, Demi's three girls were painting a rosy picture of what life with their stepfather was like. "It worked so well that I can't remember not having him there," Scout Willis told Harper's Bazaar in 2008. 

In a 2009 interview with the Daily Mail, Rumer Willis revealed that she used to have photos of Kutcher on the walls of her room, so that was a bit awkward. "He's like a friend as well as a stepdad. ... He understands more than my parents sometimes because he's closer to my age," she said.

Many years later, Rumer confessed that Kutcher's addition to the family also caused her a great deal of pain. In a 2019 appearance on "Red Table Talk," she revealed that she found it especially hurtful that Moore wanted to have a child with Kutcher so badly. "It was like, 'Oh, well. We're not enough,'" she said. Tallulah Willis spoke about how the relationship impacted her when she appeared on "Stars on Mars" (via Page Six) in 2023. "That did send me into, like, a total dumpster fire," she said. "It was really hard, and I'm still unpacking."

On Dax Shepard's "Armchair Expert" podcast, Ashton Kutcher revealed that he took a week-long solo trek to the mountains in Big Sky, Montana, after he and Demi Moore split. "I did no food, no drink — just water and tea," he recalled. "... I started to hallucinate on day two." While there, he penned letters to some of his exes in which he took accountability for his relationship wrongdoings — he didn't reveal whether Demi Moore was one of the recipients.

As for Moore, although her relapse had alienated her daughters, Rumer Willis was with her in 2012 when she had to be rushed to the hospital. Moore had become unresponsive after smoking synthetic marijuana and huffing nitrous oxide. It was Willis who called 911. On "Red Table Talk," she recalled thinking that she would also be the one who would have to call her sisters to tell them the tragic news if Moore died. But thankfully, Moore was able to get sober and reflect back on everything that went wrong during that difficult period of her life. 

"I really know that there are parts of what occurred with this relationship ending that were a level of devastating for me that wasn't really just about that relationship," Moore told ABC News. "It was really about my whole life." In his 2023 Esquire interview, Kutcher shared his own feelings about the end of their relationship. "Nothing makes you feel like a failure like divorce," he said.

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

Ashton Kutcher had gotten married and started a family with his "That '70s Show" co-star Mila Kunis by the time "Inside Out" was released in 2019. In the book, Demi Moore paints an unflattering picture of her ex-husband. In addition to accusing him of being unfaithful, she claims that he once told her, "I don't know if alcoholism is a real thing — I think it's all about moderation" (via Entertainment Weekly). After nearly two decades of being sober, Moore started drinking alcohol again. She also claims that Kutcher was cold and unsupportive after she developed an addiction to Vicodin and tried to detox. "I felt like he was angry with me for having this problem in the first place," she wrote. In a seeming response to Moore's claims, Kutcher tweeted, "I was about to push the button on a really snarky tweet. Then I saw my son, daughter, and wife and I deleted it."

While discussing the book in his 2023 interview with Esquire, Kutcher confessed, "I was f***ing pissed." However, he explained that what really bothered him was the unwanted attention the rest of his family got when it was published, saying that paparazzi pics of his children suddenly became a hot commodity. According to Kutcher, his second wife forced him to do some serious self-examination about the way he used to behave. He recalled Kunis telling him, "You were an a**hole for a good two years."

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

Months after Ashton Kutcher and Demi Moore got divorced, Kutcher showed up to watch Rumer Willis sing at Hollywood's Sayers Club. The pair were reportedly spotted sharing a warm hug after her performance. "It seemed really happy and loving — and like the two would be friendly ... no matter what," an eyewitness told People. 

In 2014, Willis told Access (via HuffPost) that she still had a relationship with her former stepdad, and Kutcher had even sent her photos of his daughter, Wyatt. She also noted that she had already surpassed the age Kutcher was when he began dating her mom and found it difficult to imagine what that experience was like for him. "That would be like me meeting someone who already had three teenage kids and kind of going into that whole situation was crazy," she said. Speaking to Esquire, Kutcher described it thusly, "That's how some teen parents must experience their twenties."

In a 2015 appearance on "The Howard Stern Show," Willis praised Kutcher for being a wonderful stepparent, and he returned the love in his 2023 Esquire interview. At the time, Willis and her sisters were still a part of his life with him suggesting they were just as awesome now as they were back then. On the "WTF" podcast, he revealed that he plans on keeping them in his life. "I'm never going to stop loving them and respecting them and honoring them and rooting for them to be successful," he stated.

Although Ashton Kutcher admitted to Esquire that Demi Moore's 2019 memoir allegations irked him a great deal, when he appeared on the "WTF" podcast in 2020, Kutcher told Marc Maron that there was no animosity between himself and his ex-wife. "It's all good; we don't hang out," he said, later adding, "There's not badness." 

While Kutcher wasn't making like Bruce Willis and vacationing with Moore, his ex-wife did end up spending some time with his current wife — Moore and Mila Kunis appeared together in a Super Bowl LVI ad for AT&T in 2022. Kunis later told ET that she had reached out to Moore about appearing in the commercial after learning that they had something in common besides Kutcher. "It was during my first collaboration meeting with AT&T that we discovered Demi was also a Fairfax High alum," she said. In the ad, the two women are attending the same high school reunion, where they both believe that they will win the "Most Admired Alum" award. However, they're left stunned when they lose to an AT&T Fiber customer. "AT&T has brought new depths to the importance of meaningful connection," Moore quipped to ET.

While Kunis and Kutcher are busy raising their kids these days, Moore has embraced a new familial role: grandmother. Before Rumer Willis gave birth to her daughter, Louetta, Moore took to Instagram to announce, "Entering my hot kooky unhinged grandma era."