Don Trump Jr.’s Proposal to Bettina Anderson Was ‘Difficult’ for Ex-Fiancée Kim Guilfoyle: ‘She Doesn’t Believe It’s Built to Last’

Kimberly Guilfoyle is taking in the news of her ex-fiancé Donald Trump Jr.’s engagement to socialite Bettina Anderson.

A source says Guilfoyle remains on good terms with Don Jr. but has concerns about the relationship. The engagement, the source claims, was difficult for her to see and reinforced her doubts.

According to the source, Guilfoyle, 56 — who was engaged to President Donald Trump’s oldest son, 47, for several years before their quiet split — still has lingering worries about his new relationship, despite the friendly dynamic they maintain.

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

The source adds that Guilfoyle believes Anderson may be drawn to the visibility and status that come with proximity to the Trump family, and claims she suspects the relationship might not exist without that connection.

The same source also alleges that the breakup took time to fully untangle.

“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 claims.

On Monday, Dec. 15, President Donald Trump announced at the White House that his eldest son and Anderson are engaged, according to a video Laura Loomer published on X.

“I’m not usually at a loss for words, because I’m usually doing the ranting and raving really well,” Don Jr. said during the announcement. “I want to thank Bettina for that one word: ‘Yes.'”

Anderson, 39, then added, “This has been the most unforgettable weekend. I get to marry the love of my life, and I feel like the luckiest girl in the world. Thank you.”

Don Jr. was previously married to ex-wife Vanessa Trump for 12 years before she filed for divorce in 2018. They share five children: Kai, 18; Donald III, 16; Tristan, 14; Spencer, 13; and Chloe, 11.

In 2018, Don Jr. began dating Guilfoyle, and they were engaged in 2020. Despite never officially announcing their split, it was reported in December 2024 that he and Anderson had been dating for about six months.

Separately, another source claims President Trump approves of Anderson, describing her appearance as a positive factor and saying he wants his son to be happy in his next partner.

That source also claims the president initially needed time to warm to Anderson, but that she ultimately adjusted to fit in with the family, describing her as having “toned down” and “mellowed out enough to be accepted.”