Kimberly Guilfoyle is speaking out, carefully, calmly, and on her own terms.
The former Fox News personality, who serves as U.S. ambassador to Greece, addressed her ex-fiancé Donald Trump Jr.’s engagement for the first time, following news of his engagement to socialite Bettina Anderson.
“I’m happy for Don,” Kimberly Guilfoyle told The New York Times in an interview published January 4. “I wish him, of course, all the best.”
A New Engagement, One Year After a Split
The comments come just weeks after President Donald Trump publicly announced his eldest son’s engagement at the White House in December 2025, roughly a year after Trump Jr.’s relationship with Guilfoyle ended.
Guilfoyle and Trump Jr. became engaged on New Year’s Day in 2022, but quietly split in 2024 after a lengthy engagement that sources later described as being “in a holding pattern.” At the time, PEOPLE confirmed that the breakup was amicable, with insiders stressing there was no major fallout between the two.
Mixed Emotions Behind the Scenes
While Guilfoyle’s public statement was gracious, sources previously told PEOPLE that the engagement was still difficult for her to process.
According to one insider, Guilfoyle remains friendly with Trump Jr. but harbors reservations about his new relationship. The source claimed she questioned whether Anderson was genuinely well-suited for him and expressed doubts about the long-term future of the pairing.
“She only wants the best for Don,” the insider said, adding that Guilfoyle struggled with seeing headlines about the engagement and wasn’t convinced the relationship was built to last.
Another source suggested Guilfoyle believed Anderson may be drawn to the prestige that comes with being connected to the Trump family, though those close to Trump Jr. have disputed that characterization.
An Amicable End — and Lingering Ties
Sources have also said that Guilfoyle and Trump Jr.’s separation took time to fully settle, noting that the pair hadn’t completely moved out of each other’s places after the split.
Despite the breakup, insiders close to the Trump family emphasized that Guilfoyle remains well-regarded within the inner circle. One source described her as intelligent, loyal, and long connected to the family, even before her relationship with Trump Jr. began.
Still, those close to the situation acknowledged that Guilfoyle is known for being direct and outspoken, traits that have long defined both her public and private persona.
Trump Jr.’s New Chapter
Trump Jr. was first linked to Anderson after the two were photographed holding hands in Florida, around the same time his relationship with Guilfoyle was coming to an end. More recently, sources have suggested that he sees parallels between Anderson and First Lady Melania Trump, noting Anderson’s modeling background and social ties in Palm Beach.
According to PEOPLE, President Trump has voiced his approval of the match, expressing that he wants his son to be happy and satisfied in his next chapter.
As for Guilfoyle, her brief but pointed remarks suggest a deliberate choice: offering goodwill publicly, while keeping the deeper emotions private, a measured response at the close of a very public relationship.
