Former Trump adviser Kimberly Guilfoyle caught the attention of fans during the 2025 Super Bowl festivities with an unexpected celebrity companion.
According to Daily Mail, the ex-fiancée of Donald Trump Jr. posed for photos with Yellowstone star Kevin Costner at the Super Bowl shortly after her split from the former president's son became public.
Guilfoyle appeared in high spirits at the event, wearing red leggings that matched the Kansas City Chiefs' team colors, paired with suede knee-high boots and a cropped black fur jacket. Costner kept his look casual in khaki pants and a white button-down shirt, complemented by light brown suede boots.
The political commentator didn't limit her celebrity interactions to Costner alone. She was also photographed with comedian Pete Davidson and actor Jaleel White during the pre-game festivities. Guilfoyle additionally spent time with Gracie Hunt, daughter of Kansas City Chiefs owner Clark Hunt.
Meanwhile, Donald Trump Jr. attended the same event with his new girlfriend, socialite Bettina Anderson. The couple was spotted at the Fanatics Super Bowl Party at The Sugar Mill the day before the game. Anderson paid tribute to Trump Sr.'s famous slogan in her Instagram Stories, writing, "Make bathroom selfies great again" while showing off her game day outfit.
The former president, Donald Trump, was also present at the Super Bowl with his daughter, Ivanka Trump, marking a historic moment as the first sitting U.S. president to attend the championship game.
Despite ending their engagement in late 2024, Guilfoyle and Don Jr. have maintained an amicable relationship. Don Jr. shared his thoughts about their split with Page Six in December, stating: "Kimberly and I will never stop caring for each other and will always keep a special bond."
The breakup hasn't hindered Guilfoyle's career advancement. Former President Trump appointed her as the U.S. Ambassador of Greece, a move that received support from her ex-fiancé. Don Jr. expressed pride in her new role and emphasized her continued involvement in his father's administration.
The former couple's split appears to have been handled with maturity and respect. Their relationship, which lasted more than six years, has evolved into a cordial professional association. Guilfoyle's appointment as Ambassador demonstrates the Trump family's ongoing trust in her capabilities.
The presence of both Guilfoyle and Don Jr. at the Super Bowl, albeit with different companions, suggests they've successfully navigated their post-breakup dynamics. While Guilfoyle socialized with Hollywood celebrities, Don Jr. spent time with Anderson, who seems to have embraced the Trump family's political messaging style.
Kimberly Guilfoyle's Super Bowl appearance with Kevin Costner marked a notable shift in her public life following her split from Donald Trump Jr.
While both attended the same major sporting event, they pursued separate social circles, with Guilfoyle engaging with entertainment figures and Don Jr. accompanying his new girlfriend, Bettina Anderson.
The former couple's amicable separation has led to continued professional collaboration, as evidenced by Guilfoyle's diplomatic appointment and their mutual support for the Trump administration.
