The headlines were breathless. On April 21, Kevin Costner was spotted having lunch with a “mystery woman” in L.A. The newly divorced star, dapper in a half-zip sweater, slim-cut pants and shades, was a gentleman, holding the door for his date.

Of course, the 70-year-old’s “date” turned out to be his assistant. But that doesn’t mean the Oscar winner hasn’t been on the prowl — or that women haven’t been lining up to date him (we see you, Kristin Cavallari!). “Right now, he’s making up for lost time and letting friends introduce him to women and flirting up a storm with any gal who shows interest in him,” an insider tells Star. “Becoming single again at his age has taken a bit of adjustment, to put it mildly. It’s taken him a while to get back into that dating mindset.”

Confidence Destroyed

No wonder. The Yellowstone star was caught off guard when his wife of 18 years, Christine Baumgartner, 51, filed for divorce in May 2023. The longtime couple, who share three kids — Cayden, 18, Hayes, 16, and Grace, 14 — cited “irreconcilable differences” and requested joint custody in separate filings. (In addition to his younger children, Kevin’s also father to Annie, 41, Lily, 38, Joe, 37, and Liam, 29, from previous relationships.)

The divorce got ugly, with the pair arguing about everything from child support to household items, despite having a prenup. At one point, Kevin claimed in court docs that he was concerned his ex would “take too many pots and pans.” In the end, Christine walked away with $200K for a new home, money to cover property taxes, a year of homeowner’s insurance and $30K a month in child support. She also quickly began a relationship with Kevin’s onetime pal, financier Josh Connor; the pair announced their engagement in January.

According to the insider, Kevin’s “confidence took a nosedive” after his divorce. “He was totally blindsided by Christine’s decision to leave him. He knew there were problems but assumed they’d work themselves out, and now he sees that was a big mistake.” After being wed for nearly two decades, he was shocked to find himself alone. “Kevin had it nice for a long time,” adds the insider, “with a pretty wife who made their home beautiful and took care of everything when he was away on long shoots.”

Starting Over

He first sparked dating rumors when he was photographed with singer Jewel during a getaway to Richard Branson’s Necker Island. But Kevin denied the romance, telling Howard Stern, “She’s beautiful and smart… It just has never happened for us.” Then there are the women coming after him. After he seemed to click with then-Today co-host Hoda Kotb, mutual friend Rachel Smith offered to play matchmaker during an ET interview. Flustered, he quipped, “I know how to meet girls if I have to.” Then Kristin Cavallari called him her “forever crush,” and begged him to hit her up. Not long after, he and also newly divorced Jennifer Lopez were spotted looking cozy in Aspen.

He’s not complaining. “Kevin needs all the reassurance he can get, and having people like J.Lo and Kristin Cavallari put the moves on him has been a boost to his self-esteem,” says the insider, adding that the Field of Dreams star “has no shortage of options. Kevin is just as popular with the ladies now as he was in his 30s. He’s kept himself in pretty good shape, and that’s to his benefit.”

Marrying Again?

Kevin finally seems to be enjoying being single — and he plans to stay that way for the foreseeable future. “Never say never, but getting married again is something that couldn’t be further from his mind these days,” says the insider. “He can’t even think about putting himself in that position — not after the way he got burned by Christine. He has no problem with marriage in general, it’s just something that’s not that important to him at this stage in his life.”

Falling in love, however, that’s another story. As the Horizon: An American Saga director told one news outlet, “I think everybody would like to be in love. There’s such a good feeling that’s associated with that. It may have to be defined in a different way, but yeah, I love the idea of that possibility.”