Donald Trump Jr.'s Ex Kimberly Guilfoyle Has 'Major Concerns' Over His Relationship With New Fiancé Bettina Anderson: 'She Doesn't Believe It's Built to Last'

Kimberly Guilfoyle reportedly isn’t sold on Donald Trump Jr.’s new engagement.

According to a source, Guilfoyle — who previously dated Trump Jr. — has lingering doubts about his relationship with socialite Bettina Anderson, despite maintaining a friendly bond with her ex.

"Kimberly knows Don well and they’re still great friends, but she has major concerns when it comes to his relationship with Bettina,” the insider shared. “The engagement was difficult for Kimberly to see and she felt it only added to her doubts about the relationship.”

Guilfoyle and Trump Jr. began dating in 2018, shortly after he and his ex-wife Vanessa Trump announced the end of their 12-year marriage. Their relationship quickly became high-profile, and by New Year’s Eve 2020, Trump Jr. reportedly proposed to Guilfoyle.

However, cracks appeared years later. In September 2024, Daily Mail reported that Trump Jr. — then still engaged to Guilfoyle — was spotted getting cozy with Anderson during an August brunch.

Despite the messy timeline, Guilfoyle and Trump Jr. have reportedly remained on good terms. Still, the source said the former Fox News host hasn’t been able to shake her concerns about his latest romance.

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

The source went on to suggest Guilfoyle believes Anderson’s interest may stem from Trump Jr.’s famous last name.

"She feels Bettina is more interested in the prestige and attention that comes with being connected to the Trump family and doesn’t think she’d be with Don if it weren’t for that," the insider added.

Complicating matters further, the source claimed Guilfoyle and Trump Jr.’s breakup wasn’t a clean break.

“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 alleged.

As OK! previously reported, Trump Jr. recently confirmed he is engaged once again — this time to Anderson — during a public moment at a White House party.

"I want to wish all of you guys an incredible holiday season, a merry Christmas, a happy New Year, and to thank Bettina for that one word 'yes.' You're going to go, you're trying to ask, you're not sure what the answer is going to be, but she said yes! That is a big win for the end of the year," Trump Jr. told guests as he praised his fiancée.

Anderson, who wore a striking red dress for the occasion, also addressed the crowd.

"What a privilege it is to be here at the White House, Mr. President. Thank you so much for hosting this incredible party, and to our first lady, these decorations, am I right? This has been the most unforgettable weekend of my life, and I get to marry the love of my life. I feel like the luckiest girl in the world, so thank you, and thank you, Mr. President," she said.