Kevin Costner has reportedly been quietly pursuing Demi Moore for several months. The Yellowstone star was among the first to offer comfort to Demi after her surprising loss at the Oscars. Despite winning both the Golden Globe and SAG awards for Best Actress, the 62-year-old actress lost the coveted Academy Award to 26-year-old Mikey Madison.

The 70-year-old Dances With Wolves star, who is single and open to new relationships, didn’t hesitate to lend a supportive shoulder to Demi, according to an insider.

“It’s clear that losing to someone less than half her age was tough for Demi,” the source says. “Kevin has been making an effort to remind her that she remains one of the most stunning women in Hollywood, though he definitely has a personal interest.”

The two have been exchanging flirtatious signals for some time. “Kevin is trying to be a true gentleman, cheering Demi on and encouraging her not to give up. He genuinely believes in her talent and thinks she’ll have another shot at the Oscar,” the insider adds.

Kevin and Demi have been friends for decades, ever since they both auditioned for Flashdance back in 1983 (though neither landed the role). Their connection grew stronger after co-starring in the 2007 thriller Mr. Brooks.

“Nothing romantic happened back then, but Kevin was clearly impressed by her. Whenever her name comes up, he speaks highly of her,” the source shares.

Now, Kevin is turning to longtime friend Billy Bob Thornton, who co-stars with Demi on the series Landman, for a little help in winning her heart.

“Billy Bob has been close to Demi for years, so he’s the perfect ally to support Kevin’s efforts. He’s been encouraging Kevin to make a move for quite some time,” the insider reveals. “Ultimately, it’s Demi’s decision whether to take things further, but friends think she should consider it.”

Adding fuel to Kevin’s motivation is the recent engagement of his ex-wife Christine Baumgartner to financier Josh Connor, who was once a friend of Kevin’s.

“Kevin’s partly driven by a desire for some payback, and he’s sure Christine would be jealous to see Demi by his side,” the source confesses. “But that’s not the only reason he’s interested — though it would definitely be an added bonus!”