Insiders Claim Kevin Costner Has ‘Always Had a Crush On’ This Oscar-Winning Actress

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

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

“There are so many gorgeous and eligible women in his circle catching his eye right now. They were off limits to him when he was married, and even in the past, he avoided dating anyone in the industry because he worried it would lead to a conflict, but he’s thrown that old rule out and is seeing all the possibilities instead,” they added, listing names such as Sandra Bullock, Witherspoon, and Angelina Jolie.

“He’s A-list, so there’s no reason 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 to stop him from asking her out.”

Now, Witherspoon and Costner were actually at the center of dating rumors back in 2023, but reps vehemently denied they were dating to EOnline. While the reps denied dating rumors at the time, they didn’t deny Costner’s alleged crush on her.

But along with Witherspoon, it seems Costner is also quite smitten with Jolie. The insider added, “And the same goes for Angelina Jolie, who he could easily get an intro to 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 single star to swoon after Jolie, because sources have recently claimed that Tom Cruise is also crushing hard on Jolie.

Now, Costner was married twice. The first was with Cindy Silva, who he married in 1978 and ended up divorcing in 1994. Ten years later, he married​ Christine Baumgartner, and they were together for nearly 20 years until they divorced in 2024. Now, Baumgartner is with one of Costner’s ex-pals, and Costner is trying out the dating scene.

Before you go, click here to see celebrity exes who will always be friends.