Kimberly Guilfoyle has responded with skepticism to the news of her ex Donald Trump Jr.’s engagement to Bettina Anderson, according to a People exclusive.
Guilfoyle, who has moved to Athens with her son in order to serve as the U.S. ambassador to Greece, dated Trump for six years. The pair were engaged at the time of their breakup in 2024, and Trump, 47, wasted no time in going public with his new girlfriend, Bettina Anderson, 39.
According to People, Guilfoyle, 56, has “major concerns” about her ex’s new relationship. A source told the outlet, “Kimberly knows Don well and they’re still great friends, but she has major concerns when it comes to his relationship with Bettina.”
“The engagement was difficult for Kimberly to see and she felt it only added to her doubts about the relationship.”
The source continued, “She only wants the best for Don, but she isn’t convinced Bettina is well-suited for Don or that what they have is the real deal.”
“Kimberly has a hard time seeing the headlines about their relationship because she doesn’t believe it’s built to last.”
The source also told People that Guilfoyle is concerned that Anderson is “more interested in the prestige and attention that comes with being connected to the Trump family” and that she would not be in a relationship with Trump without it.
Trump announced his engagement to Anderson at his father’s Christmas reception at the White House on Monday night.
In a video posted to social media by far-right provocateur Laura Loomer, Trump addressed the crowd, flanked by his fiancée and father.
BREAKING NEWS:
President Trump just announced at the White House that his son @DonaldJTrumpJr and his girlfriend Bettina Anderson are getting married! They just got engaged.
Congratulations to them both. pic.twitter.com/psb38nTGla— Laura Loomer (@LauraLoomer) December 16, 2025
“It’s not often that I’m at a loss for words ’cause we usually do the ranting and raving really well,” Trump Jr. told guests.
He went on to thank Anderson—“for that one word, yes“—before describing his nervousness prior to the proposal.
“When you go down there, it’s like, you’re gonna go, and you’re trying to ask, and you’re not sure what the answer’s gonna be. It’s always a little bit rough. But she said yes, which is a big win for the end of the year,” he said.
Trump was previously married to Vanessa Kay Haydon for 13 years. The couple had five children together. Guilfoyle and Trump began dating in 2018 and got engaged in 2020 before splitting in 2024 after news of Trump’s new relationship broke.
Guilyole was confirmed as the U.S. ambassador to Greece in September, having been nominated by President Donald Trump to the role in December 2024.
“I am profoundly grateful to President Trump and the U.S. Senate for their trust and confidence in me. It is the honor of my life to serve as the first female Ambassador of the United States to Greece,” Guilfoyle wrote in a social media post following her successful confirmation.
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