Kimberly Guilfoyle has finally broken her silence on Donald Trump Jr.’s engagement, offering a brief but carefully measured response as questions swirl about the abrupt end of one of the Trump family’s most visible relationships.
In an interview published Sunday by The New York Times, Kimberly Guilfoyle addressed her former fiancé’s engagement to Palm Beach socialite Bettina Anderson for the first time.
“I’m happy for Don,” Guilfoyle said. “I wish him, of course, all the best.”
Kimberly Guilfoyle is seen on stage before the start of the second day of the Republican National Convention at the Fiserv Forum. The second day of the RNC focused on crime and border policies.
The comment marked Guilfoyle’s first public acknowledgment of Donald Trump Jr.’s new relationship. Guilfoyle, 56, and Trump Jr., 48, were together for six years and became engaged in 2020, positioning her as a central figure in the Trump political orbit during President Donald Trump’s first term.
When the relationship ended has never been officially confirmed. Speculation intensified in September 2024 when Trump Jr. was photographed holding hands with Anderson, 39. The president’s son later announced his engagement to Anderson at the White House Christmas party, a moment that cemented the split without explanation from either side.
Soon after, People magazine reported that Guilfoyle privately doubted the relationship’s longevity. A source close to her claimed she believed Anderson was drawn more to the prestige of the Trump name than to Trump Jr. himself.
“Kimberly has a hard time seeing the headlines about their relationship because she doesn’t believe it’s built to last,” the source said, adding that Guilfoyle felt Anderson would not be with Trump Jr. without the attention that comes from the Trump family connection.
The same source said the separation was slower and messier than it appeared publicly. Guilfoyle reportedly only recently moved out of Trump Jr.’s home, with the two still sharing belongings across residences well after their engagement quietly collapsed.
“As recently as not that long ago, Kimberly and Don still hadn’t completely moved out of each other’s places,” the source said.
Trump Jr.’s romantic life has long drawn tabloid attention. He was previously married to Vanessa Haydon from 2005 to 2018, and the former couple share five children.
Guilfoyle, now serving as the U.S. ambassador to Greece, also used the interview to comment on another high-profile ex. She was married to Gavin Newsom from 2001 to 2006, before his rise to national prominence. Guilfoyle told the Times she believes Newsom is “one thousand percent” planning to run for president in 2028, despite his public caution on the subject.
Since arriving in Greece, Guilfoyle has cultivated a visible diplomatic presence, attending late-night events, high-profile gatherings, and even nightclubs as part of an unconventional relationship-building strategy, according to the Times.
