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Miscarriage, addiction, and a "do over": Inside Demi Moore's relationship with Ashton Kutcher.

It was one of those Hollywood relationships people couldn’t seem to help but weigh in on. Demi Moore and Ashton Kutcher. She, a superstar of ’80s and ’90s cinema, earnest, a style icon; he, a pin-up of 2000s sitcom television, a boyish prankster, backwards baseball caps and all.

When news of their relationship broke in 2003, their 15-year age gap (he was 25, she was 40) breathed new life into sexist cultural narratives around the whole older-woman, younger-man dynamic. Words like ‘cougar’ and ‘MILF’ clawed their way into commentary about their relationship. Or rather, about Demi.

According to The New York Times, the now 56-year-old writes in her forthcoming memoir, Inside Out, that while she largely disregarded all that criticism, there was an element of truth in there somewhere. She was drawn to Ashton’s youth, just not in the way people assumed.

To Demi — a woman who had endured two decades tinged by trauma, addiction and heartbreak — the relationship was “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 twenties.”

But that brought about moments she regrets. According to a leaked copy of the book obtained by Radar Online, Demi writes about making the “mistake” of engaging in threesomes with him and other women.

“I wanted to show him how great and fun I could be,” she writes.

She also reportedly raises allegations that Ashton cheated on her with two women in the dying days of their relationship in 2010/2011. And that he used their previous group-sex encounters to defend that behaviour: “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.”

“I felt sick to my stomach,” Moore wrote. “I knew she wasn’t lying.”

Demi’s tumultuous childhood.

As reported by The New York Times, Demi Moore’s book reveals a childhood of transience, as her family moved around the US for her father’s [Dan Guyes] job in newspaper advertising sales. Together, she and Dan supported her mother through struggles with mental illness, including her multiple suicide attempts.

Her parents’ marriage ultimately dissolved, and at the age of 13 she learned her biological father was, in fact, an Air Force airman from whom her mother had separated during the pregnancy.

“I was never supposed to know he existed,” she told Vanity Fair in 1991. “He was never involved in my life… When I was born, Danny was there. That’s why, for me, he’s my father.”

When she was 17, Dan took his own life.

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By then Demi had survived a rape (she was just 15), and had left home. At 18 she married rock musician, Freddy Moore; a marriage that ended just five years later in 1985 due to her infidelity.

On top of it all, she was grappling with newfound fame.

Demi Moore in 1987. Image: Getty.

Emilio Estevez, Bruce Willis and motherhood

After working in Europe as a pin-up model in her late teens, Demi Moore delved into acting. Her first big success, 1985's St Elmo's Fire, was a critical flop but a success at the box office.

Off screen, Demi was struggling to differentiate her appeal from her sexuality. The New York Times reported that she saw her value as tied to her body, and that "she abused alcohol and cocaine, binge-ate and obsessed over her weight" throughout the early phase of her career.

In 1986, she became engaged to actor Emilio Estevez (Martin Sheen's son, Charlie's brother), but the December wedding plans were called off. Demi then found love with action star Bruce Willis, whom she married in 1987.

Together they had three children: Rumer, born in 1988, Scout born in 1991 (and the famous bump in her mother's now-iconic Vanity Fair nude pregnancy cover shoot), and Tallulah born in 1994.

The iconic 1991 Vanity Fair cover. Image: Condé Nast.
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Between starting her family, Demi forged her career through the critically acclaimed About Last Night and the 1990 classic Ghost, in which she starred alongside Patrick Swayze. On the back of that, the early '90s brought more success with Indecent Proposal, A Few Good Men and Disclosure.

Demi leveraged her box-office baiting status to command a reported US$12.5m salary for Striptease — similar figures to what her husband was earning but record-breaking for a woman. She earned a reputation in certain sections of the media and the entertainment industry for being greedy, demanding. She even earned a tabloid nickname: Gimme Moore.

Behind all the success, her marriage was crumbling.

According to The New York Times, she writes in her book "that Willis was ambivalent about her work, which he felt took time away from their family, and he told her he was unsure if he wanted to be married".

They separated in 1998 and divorced two years later.

Ashton Kutcher and pregnancy loss.

After a series of flops, including widely panned G.I. Jane, Demi Moore backed away from Hollywood, an industry notorious for struggling to find a place for women in their 40s.

She produced, spent time with her family, and settled down with Ashton Kutcher. She reportedly writes in Inside Out that they conceived a child together prior to their 2005 marriage, but she experienced a miscarriage six months into the pregnancy. They had chosen a name for the baby: Chaplin Ray.

Ashton with Demi, Bruce Willis and their three daughters in 2003. Image: Getty.
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According to The New York Times, "She had started drinking again and blamed herself for the loss". They tried fertility treatment to no avail. Demi's drinking reportedly escalated and she began abusing prescription painkillers.

They split in November 2011, amid the allegations that Ashton had cheated on her. The first instance, in 2010, she learned of via media reports that claimed he'd slept with a woman at their home while she was out of town. The second, a year later, she learned via a Google alert, Radar Online reported. This time he'd allegedly cheated with a young woman at a friend's bachelor party. It was his and Demi's sixth wedding anniversary weekend.

“I felt sick to my stomach,” Moore wrote. “I knew she wasn’t lying.”

They divorced two years later.

Newly single, Demi spiralled further.

She experienced a seizure after smoking synthetic cannabis and inhaling nitrous oxide while partying with her daughter, Rumer, in 2012 - an incident that tested her apparently already strained relationship with her daughters.

After rehabilitation for trauma and substance abuse, she has reconciled with her girls, The New York Times reported.

“We grow up thinking that our parents are these immovable gods of Olympus,” Rumer told the publication. “Obviously, as we grow older, we start to realise how much our parents are just people.”


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