Inside Kevin Costner and Madonna’s ‘Flirtatious Friendship’: He Has a ‘Giant Soft Spot’ for Her

They famously didn't see eye-to-eye 33 years ago in Madonna's watershed concert film Madonna: Truth or Dare, but as they continue to traverse the riskiest waters of their respective careers, Kevin Costner and the queen of pop have had a below-radar friendship and mutual respect that now dates back many years.

An insider exclusively tells Life & Style they’ve been giving each other advice in recent months whilst also getting their flirt on!

"Decades after their infamous backstage encounter in Madonna's documentary, Kevin and Madonna have a flirtatious friendship going that has survived divorces, career ups and downs and a changed Hollywood that doesn't look a single bit like it did in the ‘80s when they both rose to fame,” the source says. “It helps that, against all odds, they have both managed to maintain their status as sex symbols and headlining performers right through their 60s, but the admiration runs deeper than just texts and emails.”

Kevin, 69, recently released his new film, Horizon: An American Saga - Chapter 1, the first of four Westerns he’s been developing. While reviews for the film have been hot and cold, it seems the Yellowstone actor has Madonna, 65, in his corner in this new phase of his career.

“Madonna is genuinely rooting for Kevin and his big gamble with the Horizon films, and Kevin has said nice things about Madonna to everybody who asks him about that funny moment in her film all those years ago,” the insider continues. “He clearly has a giant soft spot for Madonna and how she puts herself out there, warts and all.”

The source went on to say that Kevin was “understandably nervous” about what kind of reception Horizon would get before it was released on June 28.

“He's calling in favors from all over show business to make sure he gets enough support,” the insider adds. “But Madonna is somebody he doesn't need to ask anything of – she gets Kevin, and she's in his corner no matter what!”

Kevin's personal life has gone through some huge changes in recent months. He finalized his divorce from Christine Baumgartner in February. The former couple share kids Cayden, Hayes and Grace. The Oscar winner also welcomed kids Annie, Lily, Joe, Liam during previous relationships.

Amid his return to single life, Kevin shut down rumors that he was dating singer Jewel after they were photographed together on Richard Branson’s island in December 2023.

“Jewel and I are friends,” Kevin said during an appearance on The Howard Stern Show on Sirius XM last month. “We've never gone out, ever. She's fantastic, she's special, and I don't want these rumors to ruin our friendship because that's what we have. She's special. ... She's everything you might think, but it just hasn't happened."

“Richard Branson had been asking me for years to come down to Necker Island and so I finally did — I'm divorced all of a sudden, I'm a single father,” he added. “I said ‘Well, I guess I'll go down.’ I got on a plane with nine people. Jewel was one of them, Emma Watson was on there, and seven other people who weren't celebrities. We were the only three celebrities on an island for three days down there and then we fly back.”