Kimberly Guilfoyle reportedly has concerns about Donald Trump Jr.'s engagement to Bettina Anderson despite remaining on friendly terms with him.

Was Guilfoyle, famously brunette, ever presented with the blond-blond-brunette sequence and given the option to dye her hair? In addition to her ambassadorship, maybe she can find some solace in knowing that she never had a chance this time—and that she’s still in the running for Wife No. 3.

After years together and a quiet split, Kimberly is processing the news that her ex-fiancé, Donald Trump Jr., is engaged to socialite Bettina Anderson—and she’s got concerns. “They’re still great friends,” an insider dished. “But the engagement was difficult for Kimberly to see, and she already had doubts about Bettina.”

President Donald Trump approves of son Donald Trump Jr.'s new fiancée, Bettina Anderson, a source tells PEOPLE, explaining how she has learned to fit into the role of Trump spouse

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,

Apparently, the Trump family still enjoys being around Guilfoyle. "She's very intelligent, very smart, very loyal. Even before she and Don were together, she was close with the family. She knew Donald before she knew Don Jr., and that connection is strong. So nothing has changed," the source dished.

On March 13, 2025, news reports suggested Tiger Woods was dating Vanessa Trump, former daughter-in-law of his friend Donald Trump. Donald Trump Jr. and Vanessa Trump’s eldest child, daughter Kai Madison Trump, attends the same school as Tiger Woods' son, Charlie Woods.

Kimberly Guilfoyle was shipped off to Greece shortly after her engagement to Donald Trump Jr. ended, but a new picture makes us think she's still in bride mode.