Kimberly Guilfoyle got in her share of selfies with famous men at the Super Bowl Sunday night, at one point cozying up to Kevin Costner, while her ex-fiancé, Donald Trump Jr. was elsewhere at the NFL championship game with his new girlfriend, Bettina Anderson.
Guilfoyle, who dated President Donald Trump’s oldest son for more than six years, posted a picture of herself with Costner, 70, on her Instagram Story before the game kicked off. The 55-year-old one-time first lady of San Francisco also posted a photo of herself with former “Saturday Night Live” star Pete Davidson and actor Jaleel White.
In both photos, Guilfoyle donned a pair of tight, red leggings, suede knee-high boots and a chic cropped black fur jacket, the Daily Mail reported. It’s not clear whether Guilfoyle was rooting for the Kansas City Chiefs or the Philadelphia Eagles in Sunday’s game, though her red leggings suggests she favored the Chiefs, who sadly suffered a stunning 40-22 defeat to the Eagles.
In Guilfoyle’s photo with Costner, the “Yellowstone” actor wore a pair of khaki pants and a white button-down shirt. In true movie star style, he kept his sunglasses on.
Guilfoyle and Costner would seem to have something in common, which could give them the basis for at least a friendship. They both recently endured very public break-ups, which featured them both being “blindsided” by partners who wanted out of the relationships and who quickly moved on to romances with other people.
Guilfoyle and Trump Jr. announced the end of their engagement after his father was elected president to a second term in November. But Trump Jr.’s “dalliance” with Florida socialite and influencer Bettina Anderson was the talk of elite Palm Beach Republican circles, starting in the late summer. Even though Guilfoyle was reportedly “blindsided” by Trump Jr.’s new romance, the MAGA power couple “amicably” ended their relationship before the election, Us Weekly reported. It also appears that they kept things quiet until after the election because Guilfoyle, the ex-wife of California Gov. Gavin Newsom and a former Fox News host, also was a top fundraiser and campaigner for Trump.
In December, Trump Jr. said in a statement: “Kimberly and I will never stop caring for each other and will always keep a special bond. He also congratulated her for being nominated by his father to become the U.S. ambassador to Greece.
Meanwhile, Costner spent part of 2023 locked in a bitter divorce battle with his long-time wife Christine Baumgartner. The mother of three of his six children “blindsided” the actor and director in May 2023 by filing for divorce after 18 years of marriage. Two months later, she took a vacation to Hawaii with the “Yellowstone” actor’s friend, financier Josh Conner.
But as Baumgartner and Costner battled it out in court on child support and other issues, she repeatedly denied that there was anything romantic between her and Conner, who also was her and Costner’s neighbor in Santa Barbara. She and Connor were “just friends,” her friends would insist.
But Costner thought otherwise, with insiders telling Us Weekly that the filmmaker always “had strong suspicions that something was was going on between Christine and Josh” — before they finally went public with their romance in January 2024. Now, a year later, Baumgartner and Conner have become engaged, according to People magazine. Meanwhile, the 70-year-old Costner is still reportedly single and not dating anyone special.