Donald Trump Jr., Kimberly Guilfoyle, and Kevin Costner. Getty Images (3)
Donald Trump Jr.‘s ex Kimberly Guilfoyle spent some time with Kevin Costner at the 2025 Super Bowl.
Guilfoyle, 55, took to Instagram on Sunday, February 9, to share a photo of her with the Yellowstone star, 70, during the big game in New Orleans, which was also attended by her ex-fiancé, Trump Jr., 47, and his new girlfriend, Bettina Anderson.
Guilfoyle wore red leggings, knee-high boots and a black fur jacket while Costner kept it casual in a white button-down and khakis. In addition to meeting the Oscar winner, Guilfoyle also shared snaps of her with comedian Pete Davidson, actor Jaleel White and the daughter of Chiefs owner Clark Hunt, Gracie.
Before Guilfoyle and Donald Jr. were engaged, Donald Trump Sr.’s son was married to ex-wife Vanessa Trump. The former couple, who share five children, were together from 2008 to 2018. Later that year, Donald Jr. moved on with Guilfoyle and subsequently proposed. The pair didn’t go public with news of their engagement until his sister Tiffany Trump’s 2022 wedding to Michael Boulos.
The 2025 Super Bowl was a truly star-studded affair. In a rematch of the 2023 championship, the Kansas City Chiefs took on the Philadelphia Eagles at New Orleans’ Caesars Superdome on Sunday, February 9. (The KC squad notably won the first time around, which saw brothers Travis Kelce and Jason Kelce face off on the […]
Donald Jr. and Guilfoyle ultimately called it quits late last year.
Kevin Costner and Kimberly Guilfoyle Courtesy of Kimberly Guilfoyle/Instagram
“Kimberly and I will never stop caring for each other and will always keep a special bond,” Donald Jr. said in a December 2024 statement. “I could not be more proud of her and the important role she’ll continue to play [as U.S. ambassador to Greece].”
He continued: “She’s been an undefeated prosecutor, national TV news star, a leader of the MAGA movement and close advisor to the president. The people of Greece are getting an absolute star and now the whole world will see it more than ever.”
A source told Us Weekly that Donald Jr. ended the relationship, but that “the breakup was amicable.”
“Don and Kimberly broke up before the election and started to divide assets around the end of September,” the insider shared at the time, adding that the pair “never discussed” their breakup publicly to avoid detracting from other “important issues.”
Jaleel White, Kimberly Guilfoyle, and Pete Davidson. Courtesy of Kimberly Guilfoyle/Instagram
Donald Jr. has since moved on with Florida socialite and influencer Anderson, 38. “It’s a new relationship. He likes her a lot and has a lot of respect for her,” the second shared in December 2024 about how Donald Jr. is “smitten” by the new woman in his life.
A second insider, meanwhile, told Us how Donald Jr. ‘s romance with Anderson compares to Guilfoyle.
“When it comes to his relationship with Bettina it’s just about them,” the second source noted. “He wants a partner. She doesn’t need anything from him and just wants to be with him.”
