Donald Trump Jr and Bettina Anderson's engagement was 'difficult' for Kimberly Guilfoyle to see
WASHINGTON, DC: Kimberly Guilfoyle, former fiancee of Donald Trump Jr, is said to be processing his recent engagement to socialite Bettina Anderson with some difficulty, sources told PEOPLE, as the announcement reverberates through the Trump family and conservative circles.
It was a surprise for everyone when the president broke the news about Don Jr's engagement at the White House Christmas party on December 15, personally marking a turnaround in his life.
"I'm not usually at a loss for words, because I'm usually doing the ranting and raving really well," Don Jr said during the announcement. "I want to thank Bettina for that one word: 'Yes.'"
Up close of Bettina Anderson’s engagement ring! Don Jr did amazing!
— Kylie Jane Kremer (@KylieJaneKremer) December 17, 2025
Photo from Instagram https://t.co/eVMM8xa8VD pic.twitter.com/GtzZeJOQnd
Don Jr was previously married to Vanessa Trump for 12 years before she filed for divorce in 2018. In 2018, Don Jr began dating Guilfoyle, and they were engaged in 2020.
Kimberly Guilfoyle has major concerns on his relationship to Bettina Anderson
“Kimberly knows Don well, and they’re still great friends, but she has major concerns when it comes to his relationship with Bettina,” a source told PEOPLE exclusively.
"The engagement was difficult for Kimberly to see, and she felt it only added to her doubts about the relationship."
BREAKING NEWS:
— Laura Loomer (@LauraLoomer) December 16, 2025
President Trump just announced at the White House that his son @DonaldJTrumpJr and his girlfriend Bettina Anderson are getting married! They just got engaged.
Congratulations to them both. pic.twitter.com/psb38nTGla
"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 told PEOPLE.
"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 source added.
Don Jr's belongings are still at Kimberly Guilfoyle's
The source stated that emotional bonds between Guilfoyle and Don Jr lingered after their low-key split.
“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 claimed.
A source told PEOPLE that President Trump approved of Anderson, noting, “The president is happy with the way Bettina looks and wants his son to be satisfied in his next mate.”
Don Jr and his first wife, Vanessa, share five children: Kai, 18; Donald III, 16; Tristan, 14; Spencer, 13; and Chloe, 11.
Anderson, daughter of generous Harry Loy Anderson Jr. and Inger Anderson, has been a model in the past and is passionate about social issues.
Anderson, 38, an Ivy League graduate, has five siblings, including a twin sister.