Kimberly Guilfoyle Speaks Out on Ex-Fiancé Donald Trump Jr.'s Engagement to Bettina Anderson

Kimberly Guilfoyle has publicly addressed her ex-fiancé Donald Trump Jr.'s recent engagement to socialite Bettina Anderson, marking her first comments on the matter.

The former U.S. ambassador to Greece and Trump Jr., the eldest son of former President Donald Trump, were engaged on New Year’s Eve in 2020, announcing their engagement on January 1, 2022. However, the couple quietly ended their relationship in 2024. The news of Trump Jr.'s engagement to Anderson was revealed by his father during a White House announcement on December 15, 2025.

In an interview with The New York Times published on January 4, Guilfoyle stated, “I’m happy for Don. I wish him, of course, all the best.”

Despite her well-wishes, sources indicate that Guilfoyle is still processing the news of Trump Jr.'s engagement. A source noted that while she and Trump Jr. maintain a friendly relationship, she harbors significant concerns about his new partner. “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 explained.

Guilfoyle reportedly found it challenging to witness the engagement unfold, feeling it exacerbated her doubts about the relationship. “She only wants the best for Don, but she isn’t convinced Bettina is well-suited for him or that what they have is the real deal,” the insider added.

The engagement followed a period where Trump Jr. was seen holding hands with Anderson, shortly after which his breakup with Guilfoyle was confirmed. “Kimberly has a hard time seeing the headlines about their relationship because she doesn’t believe it’s built to last,” the source remarked.

Concerns about Anderson's motivations also surfaced, with Guilfoyle reportedly feeling that Anderson is more interested in the prestige associated with the Trump family than in a genuine relationship. “She feels Bettina is more interested in the prestige and attention that comes with being connected to the Trump family,” the source stated.

Following their breakup, emotional ties between Guilfoyle and Trump Jr. took time to unravel. “As recently as not that long ago, Kimberly and Don still hadn’t completely moved out of each other’s places,” the source revealed, noting that Trump Jr. still had belongings at Guilfoyle's home.

In December 2025, another source indicated that President Trump approves of Anderson, stating, “The president is happy with the way Bettina looks and wants his son to be satisfied in his next mate.”

The source elaborated on the family's past relationships, mentioning that they were initially pleased with both Trump Jr.'s first wife Vanessa and Guilfoyle until her public persona became too prominent. “The Trumps were happy with [Don Jr.'s first wife] Vanessa, and also with Kim at first until she became a grandstander,” the insider noted.

Anderson's initial eagerness to align herself with the Trump family reportedly raised eyebrows but has since been tempered. “At first, Bettina’s eagerness to join forces with the Trumps was off-putting to the president,” the source explained. “She has managed to mellow out enough to be accepted.”

Trump Jr. was previously married to Vanessa Trump for 12 years before their divorce in 2018. They share five children: Kai, Donald III, Tristan, Spencer, and Chloe.