Kevin Costner Reportedly Dating Around Constantly While Friends Insist He Would Get Married Again

Still fresh out of a messy divorce with Christine Baumgartner, actor Kevin Costner has reportedly been dating again.

Just a few months after his ex-wife remarried his former friend Josh Connor, the 'Yellowstone' actor has become one of Hollywood's most eligible bachelors. Costner's activities have sparked numerous rumours whenever he is seen with a new companion.

However, according to his friends, Costner isn't trying to prove anything or gather attention. Despite everything, he simply believes that love is worth the risk.

Kevin Costner's Split From Christine Baumgartner Didn't Stop Him From Looking for Love

The media attention on Costner's dating life stemmed from his highly publicised divorce from Christine Baumgartner, which ended the 20-year marriage between the two.

For several years, Costner and Baumgartner's marriage seemed ideal for Hollywood stars, and that it could withstand anything. The couple shared three children, a beautiful California home and two decades together.

However, the divorce filing came in 2023, plunging the marriage into a lengthy battle over finances, child support and property. Media scrutiny hit both sides, as court filings revealed private disagreements. Baumgartner cited 'irreconcilable differences' as a justification for the divorce.

Costner's friends said the divorce hit him hard because he never saw it coming.

The end of the marriage came with shake-ups in his hit TV series, 'Yellowstone', from which he departed in 2024 due to creative disagreements and scheduling conflicts.

By the time the divorce was finalised, his personal and professional life had entered entirely new chapters.

Despite it all, Costner hasn't given up. According to those closest to him, 'He's always out looking for love'.

The insider says the actor remains convinced that the next relationship could be different from the ones that came before. 'He still believes in romance.'

'So, dating around and seeing if he can find someone that he can have a spark with is always appealing,' the source explained. 'He's having fun dating, but he would get married again.'

Costner and Baumgartner Find New Love Elsewhere After Their Divorce

Less than two years after her divorce from Costner, Christine Baumgartner married financier Josh Connor at Santa Ynez Ranch in Santa Barbara on 18 October 2025. The ceremony occurred at a private vineyard where Baumgartner grew up.

More than 100 family members and friends attended the ceremony, including children from both sides of the blended family.

Guests described the event as personal rather than grandiose. 'It was magical-truly. The setting was gorgeous, but what made it special was the intimacy of it all. This wasn't a big production. It was authentic, heartfelt, and so very them,' a guest told PEOPLE.

On the other hand, Costner, who has reportedly been taking things slow, has been sparking rumours as he was seen with women at various points. Earlier this month, the 71-year-old was spotted with lifestyle coach Jennifer Milburn in Santa Barbara.

Witnesses described the pair as 'extremely affectionate' as they loaded several items into a grocery cart.

The sighting was reported just weeks after Costner was seen with lifestyle influencer McKenna Wesley at a screening of 'Field of Dreams' in Arizona.

Despite the speculation, a source close to the 'Yellowstone' star insists that the reports are greatly exaggerated. 'He has dated a lot of women since his divorce,' the source told the Daily Mail. 'not into trophy girlfriends in their 20s like a lot of Hollywood men his age are.'

Costner's friends described him as an old-fashioned gentleman who enjoys meeting people but isn't rushing to label anything. However, he isn't opposed to walking down the aisle if he meets another special someone later.