Don Jr. & Kimberly Guilfoyle Put On Show As Amicable Exes (& It Won't Be The Last Time)
Donald Trump Jr. and Kimberly Guilfoyle are apparently doing everything they can to convince us they're on good terms after their split. We learned of the end of their 6-year relationship and years-long engagement through Page Six insiders in December 2024. At the time, sources also revealed that Don Jr. and Guilfoyle's relationship had become shaky in the previous year, and it wasn't rare to spot them having a public spat in the halls of Mar-a-Lago. Given all this, it's unsurprising that the president elect's eldest son wasted no time finding new love with model and socialite Bettina Anderson.
Just days after news of their split broke, Don Jr. confirmed in a statement with Page Six, "Kimberly and I will never stop caring for each other and will always keep a special bond." He added, "She's been an undefeated prosecutor, national TV news star, a leader of the MAGA movement and close advisor to the president." Of course, actions speak louder than words, so the former couple is putting on public displays of their friendship too.
They seemed pretty chummy chatting on stage of the 2025 Hispanic Federation Annual Gala. In videos from the event, Don Jr.'s ex awkwardly trailed behind him as he mingled and at one point she even gave him a little shoulder rub. The exes also ran into each other at the 2025 Crypto Ball and a candlelit dinner celebrating Donald Trump. However, they likely didn't make a public show of it because Anderson was by Don Jr's. side.
Their new relationship may be more awkward than they're letting on
It's likely that Kimberly Guilfoyle will have to see her ex-fiancé parade his new romance with Bettina Anderson around at Donald Trump's inauguration on January 20, 2025. Through a January 2025 episode of the Daily Mail's "Welcome to Magaland" podcast, we learned that the former Fox News host probably earned herself a seat with the Trump family at the inauguration ceremony because of her proposed appointment as the new U.S. ambassador to Greece. While that bodes well for her political career, it may not be the best idea for Guilfoyle personally or even the ceremony at large.
As the host of the podcast and executive editor of politics at the Daily Mail, Kelly Laco, pointed out, "'Anderson is supposed to be there, so there will be some tension if both she and Guilfoyle are in the room." In fact, Guilfoyle may have created an even more awkward situation with her birthday post for Don Jr., which also served as a heartbreaking hint she can't let go. While the staunch Trump loyalist marked the occasion by sharing a collage of photos to her Instagram Stories, he celebrated with his girlfriend.
Their new dynamic is complicated by the fact that Anderson was rumored to be Don Jr.'s mistress since the Daily Mail shared photos of them cozying up in August 2024, months before their breakup was announced. Despite all the reported drama, it seems like Don Jr. and Guilfoyle's split isn't keeping them apart (and it's reminding us of Bennifer as a result).