Donald Trump Jr. and Kimberly Guilfoyle have not spoken since calling off their engagement in 2024, even as she left the Greece ambassadorship after President Trump asked her to resign.
A source told Page Six the former couple has had no communication since the split, and that the breakup was neither nasty nor bitter. They simply went their separate ways.
The update landed a day after President Donald Trump publicly downplayed any family tie to Guilfoyle. She resigned as U.S. ambassador to Greece after the White House asked her to step down amid a run of damaging claims.
Trump Jr., 48, and Guilfoyle, 57, dated beginning in 2018 and got engaged in 2020. By the time Page Six first reported the split in December 2024, they had been together nearly six years.
At the time of that December report, a source said the pair had not been getting along for about a year.
The same source described open friction at the president’s Florida club.
"Don and Kimberly haven’t been getting along over the past year. They get argumentative at Mar-a-Lago in front of people. Nothing crazy, but you know when a couple is fighting. They bicker in public."
Even so, the later account stressed an amicable end rather than a scorched private war. No lawsuits. No public mudfight. Just silence.
Trump Jr. moved on with Bettina Anderson, a 39-year-old Palm Beach socialite. The two were spotted together several times before they married in an intimate May ceremony on a private island in the Bahamas.
About 40 guests attended, including Trump Jr.’s five children with ex-wife Vanessa Trump. President Trump, 80, did not go. He said online that “circumstances pertaining to Government, and my love for the United States of America” kept him away.
That choice put official duty ahead of a family wedding and left the son’s new chapter without his father in the room.
Guilfoyle had kept ties to the Trump administration after the romance ended and served as U.S. ambassador to Greece. That chapter closed fast.
New White House press secretary Katie Zacharia confirmed the request at her first briefing. RealClearPolitics carried her remarks.
"We have asked Ambassador Guilfoyle to resign. She has been a wonderful asset to the team, and we wish her well."
Fox News reported the move followed cascading allegations of financial impropriety, improper promotion of a Greek company’s interests, and mistreatment of embassy staff. One claim held that she pressed a Trump donor to cover a $100,000 American Express bill in exchange for access.
Just the News likewise noted the donor-bill scandal as the backdrop for the resignation request. Trump had appointed her earlier in the administration after her relationship with his son ended.
Guilfoyle denied the claims and promised a fight.
"These allegations are false, and I intend to vigorously defend my name, my reputation, and my integrity."
She also reaffirmed loyalty to Trump while acknowledging the ambassadorship might be over.
Speaking to reporters, the president separated the personal history from the job performance and the unread material landing on his desk.
"She wasn't a member of my family. She, I guess, dated my son a long time ago. She was doing a good job, but we didn't like what we were reading."
That is the accountability standard voters expect: loyalty is not a shield when the paperwork looks bad. The White House asked for a resignation, praised prior work, and moved on.
After the exit, an insider told Page Six that Guilfoyle planned to find a “rich husband in Europe.” Whether that was serious talk or gossip-page color, it fit a clean break from the Trump orbit she once occupied through Trump Jr.
From 2018 dating to a 2020 engagement, public Mar-a-Lago arguments, a 2024 call-off, zero contact since, a Bahamas wedding without the president, and a forced end to the Greece posting, the record is now one of distance on every front.
Personal chapters close. Public offices still answer to the people who hired the president to clean house when the reports turn sour.
