Inside Kimberly Guilfoyle's Relationship With the Trump Family — Years After Calling Off Her Engagement to Donald Jr.
Kimberly Guilfoyle previously served as U.S. ambassador to Greece.
Oct. 14 2026, Published 3:14 p.m. ET
President Donald Trump has appeared to publicly distance himself from Kimberly Guilfoyle after she was asked to resign as U.S. ambassador to Greece amid corruption allegations.
Guilfoyle, 57, who was once engaged to Donald Trump Jr., called the accusations against her false and said she would vigorously defend her reputation. RadarOnline.com looks into her past relationship with the Trump family.
Kimberly Guilfoyle and Donald Trump Jr. Were Together for 6 Years
Donald Trump Jr. and Kimberly Guilfoyle were once engaged.
Guilfoyle and Don Jr. began dating around 2018, according to reports. At one point, they owned a $9.7million home in Florida and often made appearances together at Trump rallies.
They got engaged in 2020, but kept the announcement private until two years later.
"Falling in love with my fiancé more and more every day," Guilfoyle wrote on Instagram on Valentine's Day 2022.
Don Jr. posted a similar sentiment in 2024.
"Thanks for always being there no matter what the haters are throwing our way," he wrote at the time. "I love you."
The Breakup and the Ambassador Job
Kimberly Guilfoyle was confirmed as ambassador to Greece in 2025.
News that the couple had split surfaced in December 2024. A source told a publication at the time that they broke up before the election but kept it quiet.
Don Jr. has since married Florida socialite and model Bettina Anderson. The two were seen holding hands outside a Palm Beach restaurant in December 2024.
Trump announced Guilfoyle as his pick for the job in Greece the next day.
Reports said that the timing suggested the president wanted her out of the country. However, Guilfoyle's allies told the paper that wasn't the case.
The Reports Behind Her Exit
President Trump cut Kimberly Guilfoyle loose after damaging news report.
Guilfoyle resigned after a report alleged that she asked Republican donor Eric Deters to pay off $100,000 on her American Express card shortly before her July 2025 Senate confirmation hearing.
"Honey, please I need you to get this done for me today," she allegedly wrote in what appeared to be a text message to Deters.
Deters gave the paper what appeared to be screenshots of their messages. The Journal reported that he did not make the payment.
Guilfoyle's attorney, Jesse Binnall, disputed the messages' authenticity. The publication had also reported on her potential conflicts of interest over energy deals in the Balkans.
Donald Trump Distances Himself From Kimberly Guilfoyle
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Donald Trump said Kimberly Guilfoyle was never a 'member of my family.'
Before her ouster, Trump reacted to early reports with a brief comment.
"I just heard about it," he said at the time. "Too bad. I don't know too much, but she was always very nice."
One official told reporters the State Department's inspector general is looking into the allegations.
On Tuesday, October 14, Trump appeared to try to distance himself from Guilfoyle.
"She wasn't a member of my family," Trump told reporters outside the White House on Tuesday. "She, I guess, dated my son a long time ago."
