The engagement of Donald Trump Jr to socialite Bettina Anderson has reportedly been met with scepticism from a key figure in his life: his former long-term partner, Kimberly Guilfoyle. Sources close to the situation claim Guilfoyle, who dated the president's son for six years, is not convinced the new relationship is 'the real deal'.
Ex-Partner's Private Doubts Surface
According to an insider speaking to People magazine, the news of the engagement, which was announced at a White House Christmas reception on Monday, 'was difficult for Kimberly to see'. The source elaborated that the very public nature of the announcement at the presidential residence only intensified her reservations. 'She only wants the best for Don, but she isn’t convinced Bettina is well-suited for Don,' the confidant claimed.
The insider suggested that Guilfoyle, 56, who now serves as President Trump's Ambassador to Greece, believes Anderson's motivations may be questionable. She allegedly feels the 39-year-old Floridian 'is more interested in the prestige and attention that comes with being connected to the Trump family' and doubts the relationship would exist without that allure. Despite these concerns, the former couple are said to remain close friends, only having fully moved out of each other's homes recently.
A Glitzy White House Announcement
The engagement became public in a characteristically dramatic Trump family style. During the festive reception, President Trump himself revealed the news before his 47-year-old son took the microphone. Trump Jr, appearing emotional, thanked Anderson for saying 'yes' after a nerve-wracking 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,' he told the applauding crowd.
Anderson, radiant in a red strapless gown, addressed the room, thanking the President and First Lady Melania Trump for the 'unforgettable weekend'. She declared herself 'the luckiest girl in the world' to be marrying the love of her life. The President marked the moment by offering his future daughter-in-law a kiss and the words 'good luck'.
Ring Speculation and Rapid Rise in the Inner Circle
Scrutiny quickly turned to the engagement ring, an eight-carat emerald-cut diamond designed by Dallas jeweller Sue Gragg. Experts cited by Forbes suggested it may be larger and more valuable than the ring Trump Jr gave Guilfoyle in 2022. Anderson's integration into the Trump family has been notably swift. The pair, who began dating in spring 2024, have attended high-profile events together throughout 2025, including the Super Bowl and the President's address to Congress.
Her position was seemingly cemented last month when she took centre stage at an official White House dinner honouring Saudi Arabia, wearing a striking teal gown. MAGA insiders noted her appearance set 'tongues wagging' about imminent wedding bells. Anderson, who comes from an old-money Palm Beach banking family, was photographed alongside Trump Jr's half-sister, Tiffany Trump, and her husband, signalling her acceptance into the inner circle.
Ultimately, sources say Guilfoyle's core belief is that the romance 'isn't built to last', and she finds the constant headlines about it hard to digest. She has not publicly commented on the engagement. Meanwhile, Trump Jr appears besotted, with one friend stating he is telling people, 'This is the woman I love.' His father is also said to be an admirer, with the family viewing Anderson as 'classy' with 'impeccable fashion sense'.
