Kimberly Guilfoyle is reportedly processing her ex-fiancé Donald Trump Jr.'s engagement to socialite Bettina Anderson, while still maintaining a friendly relationship with him.

A source told People that Guilfoyle, 56, "has major concerns" about the new relationship, even as she remains on good terms with Don Jr., 47.

The source explained that seeing the engagement was difficult for Guilfoyle and reinforced her doubts about the couple's connection.

"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 said.

Guilfoyle reportedly believes Anderson may be drawn more to the prestige and attention of being associated with the Trump family than to Don Jr. himself.

Guilfoyle and Don Jr. were engaged in 2020, following several years of dating, but never publicly announced their split.

The source noted that emotional ties between the two took time to fully untangle.

As recently as late 2024, they had not completely separated their living arrangements, with Don Jr. still having many belongings at Guilfoyle's home, including clothes and shoes.

Don Jr. and Bettina Anderson Announce Engagement

Don Jr. and Anderson, 39, confirmed their engagement on Dec. 15 during a White House announcement hosted by President Donald Trump.

Don Jr. expressed his excitement, joking about being momentarily lost for words, while Anderson called the weekend "the most unforgettable" and said she feels like "the luckiest girl in the world."

The couple had reportedly been dating for about six months before publicly announcing their engagement, following Don Jr.'s divorce from Vanessa Trump in 2018.

Don Jr. and Vanessa share five children: Kai, 18; Donald III, 16; Tristan, 14; Spencer, 13; and Chloe, 11.

Despite Guilfoyle's concerns, the Trump family reportedly approves of Anderson.

President Trump is happy with the way Anderson presents herself and wants his son to be satisfied with his next partner, Yahoo said.

The insider explained that the president initially had reservations about Anderson's eagerness to join the family but now considers her more aligned with the family's expectations.