It wasn’t a dramatic breakup. There were no headlines, no public fallout. Just two high-profile figures choosing different paths, with grace.
Donald Trump Jr. and Kimberly Guilfoyle ended their years-long relationship in the fall of 2024, but the public only got confirmation months later. Now, both are moving forward, personally and professionally, while keeping a strong bond rooted in mutual respect.
“We Will Always Keep a Special Bond”
In a rare public comment shared with Page Six, Trump Jr., 47, broke his silence in December 2024:
“Kimberly and I will never stop caring for each other and will always keep a special bond. I could not be more proud of her and the important role she’ll continue to play.”
He was referring to Guilfoyle’s new post as U.S. Ambassador to Greece, a role she was nominated for by President-elect Donald Trump ahead of his second term beginning in January 2025.
“She’s been an undefeated prosecutor, national TV news star, a leader of the MAGA movement and close advisor to the president,” Trump added. “The people of Greece are getting an absolute star.”
A Private Decision With Public Implications
While the news didn’t make waves at the time, insiders confirmed that Trump and Guilfoyle called off their engagement before the 2024 election and began dividing assets in late September.
“They just had different goals,” one source said, describing the split as amicable and driven more by timing and life direction than by drama. “The breakup was mutual and so is their respect today.”
According to reports, the pair chose not to address the split publicly at first in order to avoid distracting from the election season and larger political priorities.
From Friends to Fiancés — and Back to Friends
Trump and Guilfoyle began dating in 2018 after years of friendship and announced their engagement in 2022 during the wedding of Tiffany Trump and Michael Boulos. Throughout their relationship, they remained politically aligned and often appeared together at campaign events and conservative media programs.
Despite parting ways, both continue to play active roles in the MAGA movement, with Guilfoyle now stepping onto the diplomatic stage, and Trump Jr. remaining a vocal surrogate for his father’s administration.
New Chapters, New Faces
As for what’s next? Trump Jr. is reportedly dating Bettina Anderson, a Palm Beach-based socialite. Trump and Anderson were first spotted holding hands in Palm Beach, Florida, in December 2024, and they made their relationship public in early 2025.
“It’s a new relationship. He likes her a lot and has a lot of respect for her,” a source shared. “He’s smitten.”
Guilfoyle, meanwhile, is focusing on her diplomatic role and family. She shares an 18-year-old son, Ronan, with her second husband, Eric Villency. She was previously married to California Governor Gavin Newsom from 2001 to 2006.
Trump Jr. has five children with ex-wife Vanessa Trump: Kai, Donald III, Tristan, Spencer, and Chloe.
Two Lives Moving Forward
They may no longer be engaged, but there’s no bad blood, only mutual admiration and a shared history. As Kimberly Guilfoyle takes on an international role and Donald Trump Jr. finds new footing in his personal life, one thing is clear: some bonds don’t need a title to last.
