Kimberly Guilfoyle seems to be enjoying the single life! The former fiancee of first son Donald Trump Jr. has wasted no time moving on from the breakup, as evidenced by a recent social media post. However, the question remains: who is the special man?
In an Instagram Story post, the TV personality flaunted a gorgeous bouquet of pink roses placed in an elaborate display. The floral arrangement featured about 100 stems and was draped in pearls. “Thank you 💖💖,” Guilfoyle captioned the post without revealing its sender.
The romantic display comes after Guilfoyle made headlines for her appearance at the 2025 Super Bowl. She was seen getting cozy with Hollywood veteran Kevin Costner in a post shared on social media. The pair posed for the camera, with the Yellowstone actor draping an arm affectionately around the former paegent queen.
Guilfoyle looked stylish, rocking a pair of red leggings and a chic cropped black fur jacket. She finished the look with suede knee-high boots, letting her luscious tresses fall freely. Costner, on the other hand, opted for a casual button-down shirt with pants and loafers.
The former first lady of San Francisco also took photos with stars Pete Davidson and Jaleel White, per Daily Mail. It is unsure what team Guilfoyle supported, but her red outfit indicates she was probably for team Kansas City Chiefs. Unfortunately, they lost to the Philadelphia Eagles.
Fans React To Kevin Costner & Kimberly Guilfoyle As A Couple
The sighting of Costner & Guilfoyle sent fans spiralling online, especially since both parties are single. Don Jr. was present at the Super Bowl with his new flame, Bettina Anderson. However, the former exes didn’t seem to cross paths. The first son and Guilfoyle first became an item in 2018 after his marriage to his first wife, Vanessa Trump, ended. After two years of dating, the duo got engaged in 2020 but didn’t reveal the news until 2022.
Unfortunately, in 2024, sources confirmed that the engaged couple was spending time apart. By December of that year, Don Jr. launched his relationship with Anderson. In a surprise twist, 24 hours after the launch, his father, Donald Trump, announced Guilfoyle’s nomination as the U.S. ambassador to Greece.
Costner, on his part, finalized his divorce from ex-wife Chrisitine Baumgartner last year. She has since moved on and is now engaged. With nothing stopping Guilfoyle and Costner, fans have mixed reactions.
“Good for her. She was not treated right,” one fan praised.
“Just lovely. I’m so excited that she escaped the Trump clan,” another similar comment read.
“Kimberly’s too extra for Costner,” a third fan objected.
“Costner would have ZERO interest in Giuilfoyle as a serious consideration,” this user remarked. “Maybe for a few quickies; after all, they were both left by their partner/wife not long ago.“
The status of Costner and Guilfoyle’s relationship is hearsay primarily for now. But would it be the worst thing if these two got together?
