Kimberly Guilfoyle, the former fiancée of Donald Trump Jr, is reportedly unconvinced that his new relationship with socialite Bettina Anderson will last, according to sources close to the 56-year-old. The doubts come after Trump Jr, 47, announced his engagement to Anderson, 39, during a White House Christmas Party hosted by his father, President Donald Trump.
A source told People magazine that Guilfoyle ‘only wants the best for Don’ but believes Anderson is ‘more interested in the prestige and attention that comes with being connected to the Trump family’. The insider added that Guilfoyle has only recently moved her belongings out of Trump Jr’s home, and that the former couple had not fully disentangled their lives until recently.
Trump Jr and Guilfoyle ended their six-year relationship in 2024, claiming the split was amicable. However, sources claim Trump Jr had been introducing Anderson as his girlfriend months before the breakup, and that he had privately criticised Guilfoyle’s fashion sense, saying she was ‘uptight’ and ‘always dresses so professionally’.
Despite the split, Guilfoyle was nominated by President Trump to serve as US Ambassador to Greece after the 2024 election, a role she was confirmed for by the Senate a year later. Insiders suggested the appointment was a way to ‘send Kim abroad’ and avoid any negative impact on the election. A State Department spokesperson defended the appointment, stating that President Trump had ‘full faith’ in her and that she had already strengthened US-Greece relations.
President Trump also reportedly made an awkward joke about Guilfoyle’s ex-husband, California Governor Gavin Newsom, during a 2024 fundraiser, which was met with ‘tepid laughter’ according to a book by Anna Palmer and Jake Sherman. The Independent has contacted Donald Trump Jr and Kimberly Guilfoyle for comment.
