Donald Trump Jr’s ex-fiancée Kimberly Guilfoyle is reportedly not convinced that the Trump heir’s relationship is the “real deal,” following the news of his engagement.
According to insiders, Guilfoyle, 56, “only wants the best for Don” and thinks that socialite Bettina Anderson, 39, is not “well suited” for her ex-fiance.
"Kimberly has a hard time seeing the headlines about their relationship because she doesn’t believe it’s built to last,” a source close to Guilfoyle told People. "She feels Bettina is more interested in the prestige and attention that comes with being connected to the Trump family and doesn’t think she’d be with Don if it weren’t for that.”
The insider also said that Guilfoyle has only recently moved her belongings out of 47-year-old Trump Jr’s home.
“As recently as not that long ago, Kimberly and Don still hadn’t completely moved out of each other’s places, and Don still had many of his belongings at Kimberly’s home, including clothes and shoes,” the source said.
Don Jr. and Guilfoyle ended their six-year relationship in 2024, with the pair claiming they parted amicably.
However, the source told People that Don Jr had been introducing Bettina Anderson as his girlfriend months before he divorced Guilfoyle.
“Don Jr. has always wanted to look good in his father’s eyes,” a source said. “Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach, is something that would impress him.”
Anderson is the daughter of Harry Loy Anderson Jr, who became the youngest bank president in the United States at the age of 26.
A source told People that she had initially struggled to adapt to the Trump family but eventually learned to “look beautiful, stand still and be subordinate to anything the Trumps do.”
Donald Trump announced the pair’s engagement during a White House Christmas Party, during which Don Jr gushed about his fiancée and publicly thanked her for agreeing to marry him.
An insider claimed that Don Jr was less complimentary about Guilfoyle during their relationship, though. One particularly sore spot for the ex-couple was reportedly Don Jr’s thoughts on Guilfoyle’s fashion sense.
“Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual,” another source told People last year. “The tight dresses need to go and she has been told that.”
Despite the behind-the-scenes breakup, Guilfoyle was handed a prestigious role when her ex-fiancé’s father won the 2024 presidential election.
President Trump nominated the 56-year-old to serve as the U.S. Ambassador to Greece, with Guilfoyle being confirmed by the Senate a year later.
However, insiders revealed to People that the Trumps had allegedly given Guilfoyle the job to get her out of the country.
“They are trying to send Kim abroad,” a source said. “They waited for the election to pass, but they didn’t want the split to get in the way of anything to hurt Donald in the election.”
Authors Anna Palmer and Jake Sherman claimed in their book The Hill to Die On that the elder Trump also joked about Guilfoyle’s ex-husband, who is one of the president’s arch-nemeses.
From 2001 until 2006, Guilfoyle was married to the now-California Governor Gavin Newsom.
According to People, Palmer and Sherman wrote that Trump awkwardly pointed this out during a 2024 fundraising event while tearing into Newsom’s policies.
“Kimberley, you know him, right?” Trump jabbed.
His joke received “awkward, tepid laughter,” according to Palmer and Sherman.
The Independent has contacted Donald Trump Jr and Kimberly Guilfoyle for comment.
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