Threesomes to cheating - Demi Moore’s rocky love life amid Joe Jonas rumours (2024)

RUMOURS are swirling that Demi Moore may have her eyes set on yet another young lover after developing a “flirtatious” friendship with Joe Jonas.

The 61-year-old is said to have “bonded” with the Jonas Brothers singer, 34, over lunch dates at the exclusive Hotel du Cap-Eden-Roc in Antibes, France.

Insiders told Page Six things could be turning ‘romantic’ with Joe, who recently split up with actress Stormi Bree and is amid a bitter divorce battle with wife of three years Sophie Turner.

Demi’s potential new romance with Joe, who is 27 years her junior, follows claims she has been “very selective” about who she dates despite being ‘flooded’ with offers.

A source told In Touch Weekly: “Demi gets so many offers from other Hollywood stars from literally every age bracket, and she’s very flattered by it, but she’s totally closed off to dating someone else in the industry.”

They added that the mum-of-three wants to “find love and settle down” but doesn’t want to date an actor because “there’s just not room in a relationship for two stars”.

It’s no wonder she is cautious about entering another relationship after enduring three scandal-struck marriages.

From cheating exes to feeling "shame" over having threesomes and strict rules that led to a relationship falling apart, we look back at Demi’s rollercoaster love life.

Marriage 'sabotage'

Demi was just 17 years old when she tied the knot with musician Freddy Moore, who was 12 years her senior, back in 1980.

He reportedly left his wife of nine years, Lucy, for the up-and-coming star after meeting in a nightclub. But their relationship was far from smooth sailing.

Demi cheated on Freddy the night before their wedding with a guy she met on a film set, later telling People: “I snuck out of my own bachelorette party and went to his apartment.”

In her 2019 memoir Inside Out, the actress said she got married “to distract myself from grieving the death of my father”, who died from liver cancer in 1977.

Recalling her affair, she wrote: “I felt there was no room to question what I’d already put in motion. I couldn’t get out of the marriage but I could sabotage it.”

They split up in 1983 and their divorce was finalised two years later, but Demi - whose maiden name was Guynes - chose to keep her first husband's surname.

She went on to have a shortlived romance with the actor Timothy Hutton.

'Self-destructive' fling

While filming the 1984 film No Small Affair, Demi had a fling with co-star Jon Cryer - who would later appear in Two And A Half Men alongside future husband Ashton Kutcher - during what she described as a “self-destructive” streak.

In her memoir, she claimed the actor “lost his virginity to me” and said she was “pained” thinking back to “how callous I was with his feelings”.

Later, Jon denied being a first-timer, insisting he lost his virginity in high school but said she was “totally justified making that assumption based on my skill level”.

Fans hailed him a “class act” and a “gentleman” for his response on X - formerly Twitter - in which he described having “nothing but affection for her and not a regret in the world”.

Lover impregnated ex

Demi fell for Emilio Estevez - the brother of Charlie Sheen - while filming St Elmo’s Fire in 1984 and within six months they were engaged.

She believes their relationship progressed quickly because she was “craving a family” and he “had a close relationship with his”.

He’d slept with an ex-girlfriend, lied about it, and then been forced to tell me the truth when he found out she was pregnant

Demi Moore

They spent two years dating on and off before planning their wedding ceremony but by 1986, she called off it due to him cheating on her multiple times.They ended the following year.

"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 LA," Demi wrote.

She claimed Emilio denied the affair but she didn’t believe him. Two months he had been caught out for lying about having a fling while they were on a two-week break.

“He’d slept with an ex-girlfriend, lied about it, and then been forced to tell me the truth when he found out she was pregnant,” Demi wrote.

They went to see a therapist, where she discovered she was “pretty low on [his priorities] list”, which was the final nail in the coffin for the couple.

Work ultimatum

Demi and Bruce Willis became one of Hollywood’s golden couples - and even though they divorced in 2000, she has remained supportive during his decline in health due to dementia and aphasia.

They tied the knot in Las Vegas after a four-month whirlwind romance after meeting on the set of the 1987 film Stakeout and married for a second time with Little Richard as their officiator.

She claims the “co*cky, dark and handsome” star first impressed her with his bartending moves and eagerly pursued her.

Basically he wanted to do whatever the f*** he wanted

Demi

She described feeling “a wave of schoolgirl flutters” during their early dates and said he acted like “a little boy who didn’t want to miss the ice cream truck”.

The couple had three kids together - Rumer, 35, Scout, 32, and Tallulah, 30 - but struggled to balance their careers with family life, which contributed to their divorce.

Demi claimed in her autobiography that Bruce wanted her to be a stay-at-home wife while she was winning big movie roles and was the highest-paid actress in Hollywood in 1995.

She said her “personal life was painful” at the time and filled with arguments.

In her autobiography, she recalled the poignant moment that Bruce told her, “I don’t know if I want to be married” before jetting off to film a movie.

Demi claimed he wanted the security and stability of a family but freedom to do as he pleased, adding: “Basically he wanted to do whatever the f*** he wanted.”

As a compromise they agreed not to spend more than two weeks apart and to allocate four days together inbetween.

But Demi - who called Bruce “controlling” - said she had “a very rebellious reaction” to the strict rules and deliberately broke their pact by signing up for a film project that kept them apart.

She struggled with an eating disorder during those difficult years and after their split admitted they were “more passionate about having kids than… being married”.

There were quotes from a young blonde replaying Ashton’s pickup lines. I felt sick to my stomach. I knew those words. I knew she wasn’t lying

Demi

The split was followed by a three-year relationship with martial arts instructor Oliver Whitcomb and reported flings with Spider-Man actor Tobey Maguire, Red Hot Chilli Peppers vocalist Anthony Kiedis and Colin Farrell.

'Threesomes shame'

In 2003, Demi moved on with Ashton Kutcher, who was 15 years her junior, and early into their relationship described him as her “soulmate”.

But their relationship bliss wasn’t to last, with her claiming he became “less and less present” once they tied the knot two years later.

She described going “into contortions to try to fit the mould of the woman he wanted to be his wife” and even experimented with threesomes to "show him how great and fun I could be."

Demi recalled: “When he expressed his fantasy of bringing a third person into our bed, I didn’t say no. I wanted to show him how great and fun I could be.”

Later, Demi said she was “strangely flooded with shame” after the threesomes and admitted those who got frisky with them “were good people but it was still a mistake”.

She claimed it contributed to Ashton cheating on her at least twice. She believed the threesomes “blurred the lines” of their relationship and for him “to some extent, justified what he had done”.

They split in 2011 shortly after Demi discovered Ashton cheated through a “Google alert” for a news story about his infidelity - the weekend after their sixth wedding anniversary.

She wrote: “There were quotes from a young blonde replaying Ashton’s pickup lines. I felt sick to my stomach. I knew those words. I knew she wasn’t lying."

Later, she added: “He spent the night with her, got up, and drove home to celebrate his anniversary with his wife.”

During their relationship, they also struggled to start a family - with Demi suffering a miscarriage six months into her pregnancy, which left her “lost, empty, desperate [and] confused” and failed IVF attempts.

Their divorce was finalised in 2013. Ashton said the split left him feeling like “a wholesale f***ing failure” but that he would “forever cherish” the time he spent with Demi.

Age gap lovers

After her split from Ashton, Demi moved on with another younger man. She dated drummer Sean Friday, from the band Dead Sara, between July 2013 and January 2014.

It was claimed she was introduced to the musician, then 27, while she was 51, by her daughter Rumer, who was just two years younger than her mum’s new flame.

They were pictured kissing during a romantic break in Mexico with her tattooed hunk - who sported inkings of X Men character Professor Xavier and British supermodel Twiggy.

Despite the 24-year age gap a source claimed her children were “happy for her”, telling The Mirror: “Sean’s age means he could be her daughter’s brother, not her mum’s lover but they all get along well.”

Demi kept her romances relatively under wraps until going official with Swiss chef and restaurant owner Daniel Humm in June 2022.

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They were believed to have dated for just short of a year - after first being spotted together at Paris Fashion Week - and were over by November 2022.

So does the single Striptease star have her eyes on a new prize with singer Joe - or is it a holiday flirtation? Time will tell.