Yahoo Lifestyle Kim Guilfoyle 'Kept a Watchful Eye' on Don Trump Jr. and His New Girlfriend Bettina Anderson at Inauguration (Exclusive)
In December, Don Jr. soft-launched his breakup with longtime fiancée Guilfoyle by publicly holding hands with Anderson during a romantic night out
Donald Trump Jr. was navigating his old and new relationships during his father's inaugural events.
At a few events before and after Donald Trump's swearing-in ceremony on Jan. 20, the president's eldest son was caught between his new girlfriend, Bettina Anderson, and his former fiancée, Kimberly Guilfoyle.
Sources familiar with Don Jr.'s social circle tell PEOPLE about the current dynamics between the three.
A source who attended the recent inaugural events says that Guilfoyle and Don Jr. did not cause any drama during the celebrations.
“Kim saw Don with Bettina and it was all civil. No negativity," the source tells PEOPLE. "She should be ambassador to Greece soon which is important to the administration, and she will be away a lot of the time. She is smart and dedicated. No need for animosity.”
Jacek Boczarski/Anadolu/Getty; Alex Brandon/POOL/ AFP/Getty
Kimberly Guilfoyle, and Bettina Anderson and Donald Trump Jr. at inauguration events.Despite feeling okay about where things stand, the source notes, Guilfoyle did appear interested in her ex-fiancé's movements throughout inauguration weekend.
“Kim is still very fond of Don, and kept a watchful eye out,” the source says. “She knows how beautiful and well dressed Bettina is, and there is no question that she was hurt when her romance with Don ended.”
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Donald Trump Jr. and Bettina Anderson interact with J.D. Vance at a Jan. 19 inaugural-eve ballUntil December, Don Jr. and Guilfoyle were still publicly considered a couple. The pair began dating in 2018 and got engaged on New Year's Eve in 2020.
Weeks after his father's 2024 election victory, Don Jr. was seen holding hands with Anderson — a Palm Beach model and socialite — while he was still believed to be engaged to Guilfoyle. Hours later, Don Jr.'s father nominated Guilfoyle as the U.S. ambassador to Greece, a position that would require her to live overseas.
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Kimberly Guilfoyle watches Donald Trump Jr. speak to reporters at the 2024 Republican National ConventionPEOPLE soon confirmed that Guilfoyle and Don Jr. had quietly broken off their years-long engagement, and that Don Jr. was now dating Anderson.
Since then, “Don Jr. and Kim have remained friends," says the source who attended the inauguration. "She is a loyal and consistent Trump supporter, and adviser."
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Donald Trump Jr. and Bettina Anderson at a candlelit inauguration weekend dinner on Jan. 19, 2025Around the time of Don Jr.'s changing relationship status, insiders told PEOPLE that he believed Anderson — who is part of "Waspy circles of Palm Beach" — would impress his father.
A social source now describes Anderson as social, sassy and confident — someone who isn't afraid of the spotlight.
"She knows who she is, and is proud of her looks which she flaunts," the social source tells PEOPLE of Anderson. "But she understands that she needs to look and act responsible, and never overshadow the rest of the family."
Related: Donald Trump Jr. Brings New Girlfriend Bettina Anderson to Mar-a-Lago for New Year's Eve Celebration
JIM WATSON/AFP via Getty
Bettina Anderson, center, watches fireworks with the Trump family at an inauguration weekend event on Jan. 18Another social source tells PEOPLE that Anderson would like some sort of role in the Trump administration — though the source claims she's not a workhorse like Guilfoyle, who is well-versed in politics and has long been dedicated to the MAGA movement.
The source adds that Anderson's work ethic and enthusiasm could change if she were able to find something that clicks with her.
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