Insiders Claim Kevin Costner Has ‘Always Been in Love With’ This Oscar-Winning Actress

While Kevin Costner’s reported romance with Jewel was nothing more than a deep friendship, many have wondered, “Will Costner return to the A-list dating world?” He recently spoke to Fox News about his dating criteria, saying that he wants “a person who wants to be loved, and who wants to, you know … feel like they’re at their best.” Vague, we know, but insiders say he may have a few A-list women in mind for his return to the dating scene, including a newly single, Oscar-winning actress he’s had his eye on for years. (We won’t tell you, it’s Reese Witherspoon.)

An insider recently told Life & Style Magazine that he’s “actually really excited to be free to date whoever he wants all summer.”

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“There are so many beautiful and eligible women around him who catch his eye. They were off-limits to him when he was married, and even in the past he avoided dating anyone in the industry because he was afraid it would cause conflict, but he has thrown that old rule out the window and instead sees all the possibilities,” they added, naming the likes of Sandra Bullock, Witherspoon and Angelina Jolie.

Reese Witherspoon arriving for the 49th AFI Life Achievement Award. Photo by: Priscilla Grant/Everett Collection.Reese Witherspoon arriving for the 49th AFI Life Achievement Award. Photo by: Priscilla Grant/Everett Collection.

Reese Witherspoon arriving for the 49th AFI Life Achievement Award. Photo by: Priscilla Grant/Everett Collection.

“He’s A-list, so there’s no reason why he shouldn’t have an A-list girlfriend,” they added, “There’s Sandra Bullock, who he’s known for years. Reese Witherspoon is single now and he’s always had a crush on her, there’s nothing stopping him from asking her out.”

Witherspoon and Costner were actually at the center of dating rumors in 2023, but reps vehemently denied they were dating to EOnline. While reps denied dating rumors at the time, they did not deny that Costner allegedly had a crush on her.

Angelina Jolie arriving at The Critics' Choice Awards 2018. Photo by: Elizabeth Goodenough/Everett Collection.Angelina Jolie arriving at The Critics' Choice Awards 2018. Photo by: Elizabeth Goodenough/Everett Collection.

Angelina Jolie arriving at The Critics’ Choice Awards 2018. Photo by: Elizabeth Goodenough/Everett Collection.

But in addition to Witherspoon, Costner also seems pretty smitten with Jolie. The insider added, “And the same goes for Angelina Jolie, who he easily met through his good buddy Billy Bob Thornton.” (Jolie and Thornton were married from 2000 to 2003, but remain friends to this day.)

Costner isn’t the only star with a crush on Jolie. According to sources, Tom Cruise is also said to have his eye on Jolie.

Christine Baumgartner, Kevin Costner arriving for the 94th Academy Awards. Photo by: Elizabeth Goodenough/Everett Collection.Christine Baumgartner, Kevin Costner arriving for the 94th Academy Awards. Photo by: Elizabeth Goodenough/Everett Collection.

Christine Baumgartner, Kevin Costner arriving for the 94th Academy Awards. Photo by: Elizabeth Goodenough/Everett Collection.

Costner has now been married twice. The first time was to Cindy Silva, whom he married in 1978 and divorced in 1994. Ten years later, he married Christine Baumgartner and they were together for almost 20 years until they divorced in 2024. Now Baumgartner is dating one of Costner’s ex-boyfriends and Costner is trying out the dating scene.

Before you go, click here to see famous exes who will always remain friends.

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