Trump Jr.’s Engagement Gets Side-Eye From His Former Fiancée

Donald Trump Jr.’s ex-fiancée Kimberly Guilfoyle has weighed in on his engagement to Bettina Anderson, and she does not sound convinced.

Guilfoyle, 56, who is now the United States ambassador to Greece, reportedly has “major concerns” about the new relationship. A source told People, “Kimberly knows Don well and they’re still great friends, but she has major concerns when it comes to his relationship with Bettina.”

The source added, “The engagement was difficult for Kimberly to see and she felt it only added to her doubts about the relationship.”

Trump Jr., 47, went public with his engagement to Anderson, 39, just months after splitting from Guilfoyle in 2024. Guilfoyle and Trump were together for six years and were engaged themselves before the breakup.

“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,” the source said.

According to insiders, Guilfoyle is particularly concerned that Anderson may be drawn more to the fame and attention that comes with being part of the Trump family than to Trump himself. “She would not be in a relationship with Trump without it,” the source added.

Trump Jr. made the engagement official at his father’s White House Christmas reception on Monday. Flanked by Anderson and President Donald Trump, he addressed the crowd with his usual mix of nerves and charm.

“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 the audience.

He also described the proposal, saying, “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.”

Anderson has been Trump’s partner for several months and has accompanied him to public events. The announcement of their engagement comes years after Trump Jr.’s marriage to Vanessa Kay Haydon, which lasted 13 years and produced five children.

Guilfoyle and Trump started dating in 2018 and got engaged in 2020. Their breakup in 2024 came after news of Trump’s relationship with Anderson became public.

Since her appointment as ambassador, Guilfoyle has relocated to Athens with her son. She was confirmed in September 2025 after being nominated in December 2024. Following her confirmation, she posted on social media, “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.”

Friends of Guilfoyle say she is trying to focus on her career and her child, but she is still keeping an eye on her ex. Headlines about Trump Jr. and Anderson’s romance do not make it any easier.

“Kimberly has a hard time seeing the headlines about their relationship because she doesn’t believe it’s built to last,” a source told People.

The situation highlights the mix of public spectacle and private drama that seems to follow the Trump family wherever they go.

Observers say Guilfoyle’s skepticism is understandable. Trump Jr.’s relationships have often played out in the headlines, and the timing of his engagement may raise eyebrows even among friends and family.

For now, Anderson appears confident in her relationship, while Guilfoyle focuses on her ambassadorial duties in Greece. The engagement is certain to generate more headlines in the coming months, keeping the Trump family firmly in the spotlight.

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