They have five failed marriages between them and their friendship traces back to the early 80s when they auditioned for roles in Flashdance. And now, sources say that Kevin Costner and Demi Moore have been exploring a connection outside the friend zone, amplified since The Substance star lost out on the Best Actress gong at The Oscars.
An insider says, ‘Kevin has had a crush on Demi since they first met in the 1980s - there just wasn't ever the opportunity to pursue her. But now, they’re both single and he’s seeing this as a long-awaited chance to date his dream woman. Kevin is being careful not to push too hard - he’s smart enough to know that would be a turn-off to Demi.’
The insider continues, ‘Kevin and Demi have been flirting for a while and now he’s looking to strike in the most gentlemanly way - by cheering her on and encouraging her not to give up after she lost the Best Actress Oscar to Mikey Madison. But it’s up to Demi if she wants to take the flirtation further, and friends think she definitely should.’
Rumours of a romantic spark between the Hollywood A-listers surfaced in January, with reports suggesting that both Kevin, 70, and Demi, 62, have ‘quietly told friends’ that they’re ‘open to the idea’ of a relationship. The insider also claimed that big-screen hotshot Kevin has always admired Demi and is a fan of her ‘brain, talent and stunning good looks’.
‘Don’t be surprised if they’re seen spending more time together in public very soon,’ the source teased.
It has been 14 years since Demi’s last high-profile and long-term relationship, as 2011 marked the demise of her third marriage to fellow actor Ashton Kutcher, 47, following eight years together and six years of marriage.
Amid rumours that Ashton had been unfaithful – which the Ghost actress doubled down on in her 2019 memoir Inside Out – Demi issued a statement which read, ‘It is with great sadness and a heavy heart that I have decided to end my six-year marriage to Ashton. 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.’
Demi had not long celebrated her 18th birthday when she got married for the first time. In February 1981, she tied the knot to musician Freddy Moore, who was 30 at the time. Their divorce was finalised in 1985, and she revealed in her memoir that she had been unfaithful to Freddy, most shockingly the night before they said, ‘I do.’
After a brief and failed engagement with actor Emilio Estevez, Demi – who has long been hailed as one of the sexiest women alive - moved on with Bruce Willis, the father of her three daughters, Rumer, 36, Scout, 33, and Tallulah, 31. They were married for just over 10 years until 1998 and their divorce was finalised in 2000. Demi remains close to her ex-husband and his wife Emma Heming Willis, particularly through the award-winning actor’s battle with frontotemporal dementia.
And, while Demi previously voiced that she was ‘plucked out as a bit of a poster girl’ for dating younger men, sources say that her inner circle are encouraging her to mix it up.
The insider shares, ‘It’s no secret Demi prefers dating much younger men, which could be a barrier with Kevin. But a lot of people in her life are urging her to try something new. Clearly dating younger guys has not worked out well for her and a lot of her friends think it would actually be really good to break that pattern. At this point, she’s got zero love life. Part of the issue is that she was so hurt by Ashton that she’s never let herself be vulnerable again.’
Meanwhile, decorated actor Kevin – who co-starred with Demi in the 2007 thriller Mr Brooks - has dealt with his own share of heartache. In May 2023, after almost two decades of marriage, his second wife Christine Baumgartner filed for divorce. Proceedings turned notoriously acrimonious, with Christine reportedly seeking $248,000 in child support – the pair are parents to Cayden, 17, Hayes, 16, and Grace, 14 – and she previously failed to move out of the California home she shared with Kevin, in what was a breach of their prenup. In February last year, their divorce came to a settlement, but the details of their financial agreements have not been disclosed.
Opening up about the divorce, Kevin said, ‘That’s a crushing moment. It’s powerful. It hurt, but I go forward. I can’t wilt like a daisy. I have to go forward. I have to continue to be who I am, and keep a special eye on who [my children] are.’
In addition to his teenage children with Christine, the Yellowstone star also shares Annie, 40, Lily, 38, and Joe, 28, with his first wife Cindy Silva. The pair met in the mid-seventies at college and got married in 1978 before separating 16 years later. Kevin also had a brief relationship with Bridget Rooney, who is the mother of his 28-year-old son Liam.
Now, the source says that Kevin is not pursuing Demi with a full-steam-ahead approach, but that hasn’t stopped him from pondering on their potential.
The source says, ‘Kevin has obviously suffered a huge betrayal himself. He was devastated when Christine left him, and no doubt he’s out to prove himself. Landing Demi would go a long way to shoring up his ego, but he insists that’s not the motivator for him. He’s playing the long game here and is fine to get to know her as a friend until she gives him the go-ahead to take it further.
‘But make no mistake, that is the goal for Kevin. He would love to romance Demi believes he has so much to offer in terms of life experience and intellect. Dating him could be the challenge Demi needs.’