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A Complete Timeline Of Demi Moore’s Relationships

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This feature contains references to addiction and miscarriage.

Demi Moore is one of the most iconic actors in Hollywood. In fact, according to CelebrityNetWorth.com, the “Ghost” star was once the highest paid female star in the mid-1990s. The husky-voiced beauty officially rose to fame in 1985, with the role of the troubled Jules in Joel Schumacher’s post-college drama, “St. Elmo’s Fire.” The role anointed her as an official member of the Brat Pack — AKA the most beloved young celebrities of the 1980s. Yet while other members of the Pack struggled to find movie roles later on in life, Moore continued to thrive in the business with roles in films like “A Few Good Men,” “Indecent Proposal,” and “Striptease.”

As The New York Times noted, for a while, Moore appeared to step back from acting to focus on raising her three children. Even though she was no longer starring in cinematic hits, the “G.I Jane” star still managed to stay in the spotlight. Yet instead of focusing on her film career, the public became extremely interested in her private life. This was especially the case for her romantic relationships, which have been heavily scrutinized since the beginning of her career. From her 12-year-long marriage to Bruce Willis to her messy romance with Ashton Kutcher, there’s a whole lot to unpack when it comes to the actor’s relationship woes. So without further ado, let’s take a look at all of Moore’s most significant romances throughout her life. It’s a wild ride, so hold on tight.

First love with musician Tom Dunston

Demi Moore’s first real relationship kicked off when she was just 15-years-old. In her memoir “Inside Out” (via USA Today), Moore admitted that she was going through a lot of turmoil at this age due to the toxic relationship she had with her parents at home. Fortunately for Moore, she was able to find solace in musician Tom Dunston’s arms — he was 28-years-old at the time, making him 13 years her senior.

In her memoir (via Amazon), she wrote of the relationship, “He was an attractive 28-year-old with a gentle presence. He immediately made me feel at ease. We started hanging out, and one night when we were alone, I stopped to take off my clothes. Tom stopped me. ‘You don’t have to do that,’ he said. ‘We can just be together.'”

While their age gap may have been inappropriate, Moore described her relationship with Dunston as highly comforting. However, the “Disclosure” star may have already been ready to move on with a different fella. Another older musician named Freddy Moore. 

A failed marriage to rock star Freddy Moore

Apparently, Demi Moore has a thing for musicians. The actor began dating guitarist Freddy Moore when she was still a teenager. 16-years-old to be exact. According to her memoir “Inside Out” (via Daily Mail), the musician was 29 when they began seeing each other. If the age gap wasn’t enough of a red flag, the fact that he was already married at the time might have been. Despite all the obstacles in their way, the “Ghost” star took the leap and pursued a relationship with him head-on, and a year later the pair married one another. Needless to say, their romance didn’t work out in the long run.

In her memoir (via US Weekly), Demi wrote, “I was a self-absorbed teenager who hadn’t been raised with a lot of respect for the institute of marriage, and I jumped into life with Freddy without, I’m sorry to say, much concern for his wife.” Per the Daily Mail, she had intense doubts about the relationship. So much so that she abandoned her own bachelorette party to cheat on her soon-to-be hubby, in a bid to sabotage the union.

The couple was together from 1980 to 1985, per the outlet. At the very least, she gained something important from the marriage: her surname, which she maintained throughout her career and other marriages. According to The Guardian, her real name is Demi Gene Guynes. 

Puppy-love with Jon Cryer

In 1984, Demi Moore and Jon Cryer played love interests in the rom-com, “No Small Affair.” In the movie, Moore is a sultry nightclub performer, while Cryer is the gawky-but-lovable photographer who drools over her. Life began to mirror art because, behind the scenes, Cryer turned Moore into the center of his universe. Although they eventually began to date, the two were both on completely different pages. During an interview with “The Meredith Vieira Show,” he explained that he may have been just a little more involved than she was. He said, “I went to her house, and her housekeeper greeted me. And I asked, ‘Oh, where’s Demi?’ And she said, ‘She’s out with her boyfriend.’ And I said, ‘But I’m her boyfriend.'”

In her memoir (via Daily Mail), Moore even claimed to have taken Cryer’s virginity during the relationship — something that she ultimately came to regret. “It pains me to think of how callous I was with his feelings,” she wrote. “That I stole what could have been such an important and beautiful moment from him.”

Fortunately, Moore doesn’t need to hold onto that guilt any longer. On Twitter, the “Two and a Half Men” star officially, and hilariously, put the rumors to rest. He said, “While I’m sure she was totally justified making that assumption based on my skill level (and the stunned look on my face at the time), I had actually lost my virginity in high school.” 

Her tumultuous engagement with Emilio Estevez

Demi Moore had once been in a whirlwind romance with her fellow “Brat Pack” member, Emilio Estevez. According to In Style, the couple dated from the time they began shooting “St. Elmo’s Fire” in 1985. In the early days, it seemed as though the lovebirds were unbreakable, and they got engaged after just six months together. But all hell broke loose when Moore discovered that Estevez had been cheating on her. 

The “Striptease” star wrote about the alarming discovery in her memoir (via Yahoo! News), stating that the timing was especially painful. “Emilio and I had in fact just mailed out the invitations for our wedding when a friend told me she had seen him out with someone else in L.A.,” she wrote. “He denied it, of course, but I was having a hard time trusting him.” This was particularly understandable given that Moore claimed that just a few months earlier, she caught Estevez lying about having slept with an ex-girlfriend. He fessed up only when he discovered the other woman was pregnant.

When she discovered that she was fairly low on her beau’s priority list, Moore broke things off with Estevez before the wedding. Despite the drama, they were apparently able to remain friends and it was actually at Estevez’s premiere party where she met the man who would become her future husband, Bruce Willis, per In Style.

Demi Moore and Rob Low literally had perfect chemistry

Demi Moore and Rob Lowe never had a full-blown relationship with one another, but according to Moore’s memoir (via ET) the two may have hooked up once. The beloved Brat Pack members met on the set of “St. Elmo’s Fire” back in 1985, and have remained good friends ever since. Back in the ’80s, Lowe was quite the jokester, and he used to tell Emilio Estevez (Moore’s lover at the time) that he and Demi had a little something going on. Moore recalled the banter in her book (via Yahoo! News), “The worst part of this was that at the time I was seeing Emilio Estevez, and Rob and Emilio were friends,” she wrote. “Rob would call up Emilio and say, ‘Hey, guess what I did all day? I spent the entire day in bed with Demi. Ha-ha.'”  

According to Moore, it would become more than a silly joke to rile up Estevez. While filming the steamy rom-com “About Last Night,” she and Lowe reportedly spent the night together. While they never took their relationship to the next level romantically, Moore played a major role in Lowe’s life. In fact, according to Lowe in an interview with “The View” (per ABC News,) Moore is the one who inspired him to get sober after she had sworn off drugs and alcohol in the mid-’80s. According to Today, he has been sober for over 30 years.

If you or anyone you know is struggling 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).

Moore’s 12-year marriage to Bruce Willis

Demi Moore and Bruce Willis had one of the most publicized romances in Hollywood history. That potentially had something to do with the couple being two of the highest-paid actors of their time. The pair met at Emilio Estevez’s premiere party for his 1987 film “Stakeout,” and they apparently began planning their future together not long after. Speaking to Vanity Fair, Moore explained that she was drawn to Willis’ no-nonsense approach to romance. “Most men, I found, played games, like ‘I’m not going to let you know I like you, babe,'” she told the publication. “But he was straight out about who he was. I needed to be loved and embraced. Bruce wanted to nurture me as much as I wanted to nurture him.”

Per People, they were said to be living different lives by the end of their marriage and there were rumors of infidelity on both sides. For her part, Moore suggested in her memoir (via ET) that she suspected Willis of cheating on her. However, their children kept them together. 

Although the couple didn’t work out in the long run, it’s safe to say that they genuinely adored one another. To this day, they are still great friends and co-parents to their three daughters, Rumor, Scout, and Tallulah. In 2022, Moore was publicly supportive of Willis amid his aphasia diagnosis.

A rumored penchant for younger men

Following Demi Moore’s messy split from Bruce Willis, the star was at a crossroads. The couple had been together for more than a decade, and it took a lot of strength for her to get back out there again. In “Inside Out” (via Fox News) she wrote that although the breakup was difficult at first, she found strength in coming out the other side better connected to her ex-husband and their children. She eventually also found the courage to date again. 

By 2003, the star was rumored to have dated a flurry of high-profile younger men. According to Daily Mail, that list was said to have included Leonardo DiCaprio, Owen Wilson, and Colin Farrel. Whether those rumors were actually true or not was anyone’s guess. Moore did, however, appear to have had a serious relationship with martial arts instructor Oliver Whitcomb, and was reported by the outlet to have moved in with him until their breakup in 2002. 

A year later, she’d meet and start dating the man who would become her third husband — “That ’70s Show” star, Ashton Kutcher. Unfortunately for Moore, it wasn’t all smooth sailing from then on.

Her disastrous marriage to Ashton Kutcher

Demi Moore’s relationship with Ashton Kutcher started as a dream come true. In her memoir (via ET), the star wrote that the two enjoyed an instant connection. “He was 25. I was 40. But I’m telling you: we couldn’t feel it,” she wrote. “We were totally in sync, from our very first conversation.” However, over time, the two faced various obstacles together. After years of sobriety, Moore experienced a relapse. At six months pregnant, she also experienced a heartbreaking miscarriage, per the outlet. 

Things took a further turn for the worse when Kutcher allegedly began cheating on Moore in what she supposed was an effort to wriggle his way out of the marriage. In “Inside Out” (via Entertainment Weekly,) she wrote that the “Dude, Where’s My Car?” actor cheated on multiple occasions with younger women. “Every one of his actions was saying ‘please don’t love me,” she wrote of her ex-husband. “But, unfortunately for both of us, I did.”

According to Us Magazine, the couple was together from 2003 to 2011. At the time of their split, Moore released a statement to the Associated Press (via The Washington Post) suggesting how heartbroken she was over the decision. Though clearly devastated, she made it clear that the decision was a necessary one. “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.”

If you or anyone you know is struggling 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).

Keeping it short and sweet with Harry Morton

For a short window of time, Demi Moore was romantically tied to the popular restaurant owner, Harry Morton. According to Hollywood Life, the successful entrepreneur was rumored to have been in relationships with the likes of Lindsey Lohan and Paris Hilton. While Morton is best known for creating the trendy 1999 restaurant Pink Taco, his family founded The Hard Rock Hotel and Morton’s The Steakhouse, and he was once an owner of The Viper Room, per Los Angeles Times.

According to People, the couple began their brief romance in 2013. Although the pair only dated for a handful of months, they were said to have had a blast together. “Demi was very giddy during her date with Harry,” a source spilled to People. “She was really into him and seemed to very much enjoy his company.”

They eventually fizzled out but remained on good terms with one another, according to E! News (via UPI). Yet tragedy struck when Morton, who was only 38, unexpectedly died in 2019. According to E! News, Moore attended his memorial service along with Lohan and Jennifer Anniston.

Finding a rhythm with drummer Sean Friday

In 2014, Demi Moore was spotted on vacation in Mexico with Sean Friday, drummer for the rock band, Dead Sara. According to UPI, the musician was 27 during the height of their romance, making him 24 years younger than the “Ghost” star, who was 51 at the time. But hey, more power to her. Still, the age gap attracted attention and Moore once again found herself the focus of tabloid scrutiny for taking on younger lovers. Speaking to W Magazine (via Marie Claire) in 2009, she rolled her eyes at the idea. “I’m certainly not the first person to have a relationship with a younger man, but somehow I was plucked out as a bit of a poster girl,” she stated.

Despite their age gap, the two were fairly serious and dated for over a year, per E! But all good things must come to an end, with Friday and Moore’s romance being no exception. Despite moving on from her whirlwind romance with Friday, Moore seemed to be on a musician kick at the time, because she went on to reportedly date a familiar face …

Did Demi Moore date Nick Jonas?

Yep, you’ve read that right. According to Radar Online, Demi Moore allegedly dated the beloved Jo-Bro, Nick Jonas, with the pair reportedly began hooking up in 2018. There may have been a rather large age gap between the two, considering Moore is 30 years his senior, but it’s pretty evident that the “Scarlet Letter” actor has a habit of dating outside of her age range. Jonas is no different, considering his current wife, Priyanka Chopra, is ten years older than him.

Moore has been made the butt of the joke for many years over the fact that she prefers to date younger men. Yet, according to the “Indecent Proposal” star, there is a huge double standard in Hollywood, considering the long list of male actors who date much younger women. And for whom, no one appears to bat an eye. “It’s so silly,” she said during an interview with ABC News. “I think part of it is we’ve been conditioned societally to look at the value of a woman being tied to her fertility. Like, what would an older woman have to offer?”

The romance between Moore and the “Jealous” singer apparently didn’t amount to much. But fear not, because she seemed to have found herself a new man: 46-year-old Swiss Chef, Daniel Humm. Free gourmet meals on the reg? Yes, please!

Love with world-renowned chef Daniel Humm

According to Page Six, by 2022, Demi Moore had been dating famous Swiss chef Daniel Humm for a number of months. Per his Instagram, Humm owns the restaurant Eleven Madison Park, and he appeared to be smitten with the star. In a post shared at the beginning of May that year, he paid tribute to his girlfriend, writing, in part, “Couldn’t be more proud of you. Your endless beauty is deeply soulful.”

US Weekly reported that the couple share a great deal in common and vibed with each other right away after being introduced by mutual friends. Meanwhile, a source suggested to Page Six that the relationship was going from strength to strength. “They are really hot and heavy at the moment,” the source claimed to the outlet. “Daniel works long, hard hours at his restaurant Eleven Madison Park, but they still often take time to have Demi join him for romantic dinners there.”

Hopefully dating a chef will be the cure to Moore’s relationship woes. After all, actors and musicians aren’t exactly renowned for making stable partners, but a chef could be just the change that the star needs for a well-deserved happy ending. Regardless if they work out or not, the “Ghost” star will be just fine with or without a lover. She is Demi Freakin’ Moore, after all!




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