Donald Trump Jr and Bettina Anderson's engagement was 'difficult' for Kimberly Guilfoyle to see

A source also said that while Kimberly Guilfoyle wants the best for Donald Trump Jr, she isn’t convinced Bettina Anderson is well-suited for him
Donald Trump Jr was engaged to Kimberly Guilfoyle prior to his relationship with Bettina Anderson (Getty Images)
Donald Trump Jr was engaged to Kimberly Guilfoyle prior to his relationship with Bettina Anderson (Getty Images)

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.'"



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."



"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.

Donald Trump, Jr and Kimberly Guilfoyle attend the DC premiere of the film,
Donald Trump Jr and Kimberly Guilfoyle attend the DC premiere of the film 'Death of a Nation' at E Street Cinema in Washington, DC (Shannon Finney/Getty Images)

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.”

Donald Trump Jr., son of U.S. President Donald Trump and his girlfriend Bettina Anderson follow behing U.S. President Donald Trump on the South Lawn of the White House on July 29, 2025 in Washington, DC. President Trump returned to the White House with his family after a trip to Scotland that was part vacation, part work, as he stayed at his Trump Turnberry golf course, followed by Trump International Golf Links in Aberdeenshire, from July 25 to 29. (Photo by Anna Moneymaker/Getty Images)
Donald Trump Jr, son of President Donald Trump, and his girlfriend Bettina Anderson follow behind US President Donald Trump on the South Lawn of the White House in Washington, DC (Anna Moneymaker/Getty Images)

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.

PALM BEACH, FLORIDA - DECEMBER 15: Bettina Anderson attends
Bettina Anderson attends 'A Retro Chic Afternoon' hosted by FIGUE, at Designer and CEO, Liz Lange, celebrating her inaugural collection with the brand and the book, 'Slim Aarons: Style in Palm Beach, Florida' (Rodrigo Varela/Getty Images)

Anderson, 38, an Ivy League graduate, has five siblings, including a twin sister.

GET BREAKING U.S. NEWS & POLITICAL UPDATES
STRAIGHT TO YOUR INBOX.

MORE STORIES

The post appeared to reference Bud Light's 2023 partnership with Dylan Mulvaney, which sparked a boycott among many conservatives
39 minutes ago
The remarks quickly changed the mood inside the venue. Audience members reportedly responded with boos, and some concertgoers chose to leave before the show ended
54 minutes ago
Dissenting from the court's unsigned ruling, Sonia Sotomayor said her colleagues ignored lower-court findings, risking election 'chaos'
1 hour ago
President Donald Trump is not alone in facing scrutiny over public absences; former President Joe Biden faced similar questions during his presidency
1 hour ago
Jill Biden also joked that the former President is forgetting the event was organized to discuss her memoir during the humorous exchange.
1 hour ago
Richard Gere called Trump presidency the ‘darkest moment’ in a fiery speech
1 hour ago
The 90-foot UFC arena is being built for a June 14 event marking America's 250th anniversary and Trump's 80th birthday
1 hour ago
Tensions emerged earlier this year after Pope Leo made remarks emphasizing peace and diplomacy amid international conflicts
2 hours ago
Protesters are demanding the immediate cancellation of the project, citing extensive environmental damage, land theft, and government corruption
2 hours ago
Jill Biden’s memoir sheds light on awkward encounter with Melania Trump during power transfer
2 hours ago