Donald Trump Jr's Ex-Fiancée Kim Guilfoyle 'Isn't Convinced' His Engagement with Bettina Anderson Is 'Built to Last'

Kimberly Guilfoyle has mixed thoughts about the engagement news of her ex-fiancé, Donald Trump Jr, to socialite Bettina Anderson. According to People, while Guilfoyle and Trump Jr remain on good terms, she reportedly has some reservations about his relationship with Anderson.

'The engagement was difficult for Kimberly to see, and she felt it only added to her doubts about the relationship,' a source told the magazine.

Not Built to Last

An insider claimed that the 56-year-old diplomat and former prosecutor, who was previously engaged to US President Donald Trump's oldest son, has longstanding concerns about Anderson despite maintaining a friendly dynamic with Trump Jr.

'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. 'Kimberly has a hard time seeing the headlines about their relationship because she doesn't believe it's built to last.'

The source added that Guilfoyle thinks that Anderson's priority is the attention and prestige that comes with the Trump family connection. She also allegedly believes that Anderson would not have pursued a relationship with Trump Jr without that privilege.

It was also noted that the emotional attachment between Guilfoyle and Trump Jr took time to fade after their quiet breakup in December 2024. Guilfoyle and her representatives have yet to respond publicly to the claims.

Kim and Don's Past

Romance between Guilfoyle and Trump Jr became public after his ex-wife, Vanessa Trump, confirmed her divorce filing in 2018.

The couple secretly became engaged in December 2020, only making it public in January 2022. The end of their engagement was confirmed last year after Trump Jr was spotted holding hands with Anderson.

'It's a friendly split between Kimberly and Don Jr,' an insider claimed at the time, noting 'they've had a very long engagement [and] it was kind of in a holding pattern.'

According to reports, Trump Jr and Anderson had already been seeing each other for six months before his breakup with Guilfoyle was announced.

Don and Bettina's Engagement

The engagement between Trump Jr and Anderson was announced by President Trump himself during a Christmas reception at the White House on Monday, 15 December.

'I'm not usually at a loss for words, because I'm usually doing the ranting and raving really well,' Trump Jr said after his father gave him the floor to talk about the engagement. 'I want to thank Bettina for that one word: "Yes."'

Anderson, on the other hand, shared that she just had a very memorable weekend, saying she felt lucky to be marrying the love of her life.

Trump Jr was previously married to Vanessa for 12 years before she filed for divorce in 2018. The former couple share five children: Kai (18), Donald III (16), Tristan (14), Spencer (13) and Chloe (11).

People previously reported that President Trump gave his approval to Anderson. According to a source, 'The president is happy with the way Bettina looks, and wants his son to be satisfied in his next mate. '

The newly engaged couple have yet to reveal their wedding plans.