Kimberly Guilfoyle's Reported Take On Don Jr. Engagement Is More Emotional Than She's Letting On

A year ago this month, we learned that Donald Trump Jr. and Kimberly Guilfoyle had called it quits. Now, Don Jr. is already engaged to the alleged mistress he reportedly ditched her for. That's a pretty tough break for Guilfoyle. And while she's putting on a brave face on social media, things may be different behind closed doors.

On December 15, Don Jr. took the stage at a White House holiday party to announce that he had popped the question to socialite Bettina Anderson. In true Guilfoyle fashion, she didn't miss a beat taking to social media to show how successful, unbothered, and utterly Facetuned she was in the wake of the big news. The next two days, she posted Instagram photos of herself hard at work as the U.S. ambassador to Greece, posing with world leaders while donning a full glam look. 

But how is she really feeling about news of her ex-fiancé's new fiancée? Well, according to an insider, she's feeling about as good as you might expect. "Kimberly knows Don well and they're still great friends, but she has major concerns when it comes to his relationship with Bettina," the source told People, adding, "The engagement was difficult for Kimberly to see and she felt it only added to her doubts about the relationship."

Kimberly Guilfoyle and Donald Trump Jr. started dating in 2018 before getting engaged in 2020. They announced their breakup in December 2024, and Don Jr. made it official with Bettina Anderson at the Mar-A-Lago Christmas party that month. With a timeline like that, it's unsurprising that Guilfoyle has doubts about her ex's new relationship. "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 explained to People, adding, "Kimberly has a hard time seeing the headlines about their relationship because she doesn't believe it's built to last." 

According to the insider, Guilfoyle thinks Anderson might be in it with Don Jr. for his high-profile status. Considering the fact that Anderson's Instagram bio says, "I'm just your typical stay at home mom ... only I don't do household chores ... or have a husband ... or have kids," it's hard to disagree with Guilfoyle's alleged assessment of the situation.

And many people are on the same page. It was immediately clear that Don Jr. can't shake his shady dating reputation with his latest proposal. Folks online have expressed their doubts about Don Jr. and Anderson's future together. In fact, even Donald Trump gave Anderson a suspicious response after the engagement news, replacing the typical "congratulations" with a more ominous "good luck." So, whenever Guilfoyle feels sad about Don Jr.'s engagement, hopefully she takes heart in the fact that many folks think it's doomed.