Kimberly Guilfoyle, who previously dated Donald Trump Jr., expressed dismay following his recent engagement announcement to Bettina Anderson, though she harbors hopes for his happiness.

The 47-year-old Trump Jr. revealed his engagement to Anderson, a socialite, on Monday, marking a new chapter after his six-year relationship with Guilfoyle, who is 56.

According to a source speaking with People, Guilfoyle found the announcement challenging, particularly given its public nature.

“While she wishes Don well, Kimberly harbors doubts about Bettina’s compatibility with him and questions the authenticity of their relationship,” the insider revealed.

Guilfoyle reportedly suspects that the 39-year-old Anderson is drawn more to the allure and attention of being associated with the Trump family, and questions whether her interest in Trump Jr. would persist without that connection.

Don Jr’s ex now serves as President Trump’s ambassador to Greece. The friend told People that the former couple remain close. 

‘Kimberly knows Don well and they’re still great friends, but she has major concerns when it comes to his relationship with Bettina,’ the ally said, adding that they had not completely moved out of each other’s homes until recently.

Seeing the pair announce the engagement at the White House ‘only added to her doubts about the relationship.’

Kimberly Guilfoyle is reportedly not ‘convinced’ by Donald Trump Jr’s new engagement

Trump Jr, 47, announced his engagement to socialite Anderson (both pictured left) on Monday

Ultimately, Guilfoyle thinks the relationship isn’t ‘built to last’ and ‘has a hard time seeing headlines’ about the romance. 

Guilfoyle has not commented publicly on her ex’s engagement and did not respond to People’s request for comment.  

The engagement was revealed by the president during a Christmas White House reception on Monday night. 

After embracing his father, Trump Jr took to the microphone to tell attendees that he was at ‘a loss for words.’ 

‘I want to thank Bettina for that one word: yes!’ he joked. 

The president’s eldest son revealed he was unsure whether his new bride-to-be would actually accept his proposal as he got down on one knee. 

‘When you go down there, it’s like, you’re gonna go, and you’re trying to ask, and you’re not sure what the answer’s gonna be. It’s always a little bit rough. But she said yes, which is a big win for the end of the year.’ 

The crowd at the White House then applauded and cheered as the 38-year-old Anderson spoke, first thanking the president and First Lady Melania Trump. 

The pair made the news public at the White House with Don Jr’s father on hand

Guilfoyle thinks the relationship isn’t ‘built to last’ and ‘has a hard time seeing headlines’ about the romance

‘Wow, what a privilege it is to be here at the White House, Mr President, thank you so much for hosting this incredible party, and to our First Lady, these decorations, am I right, aren’t they unbelievable?’ 

Anderson looked elegant in a red, strapless gown as she beamed about her engagement. 

‘This has really been the most unforgettable weekend of my life, and I get to marry the love of my life, and I feel like the luckiest girl in the world!’

President Trump then offered his future daughter-in-law a kiss and two words – ‘good luck’ – as the crowd applauded again. 

It was later divulged by Forbes that Anderson’s ring was an eight-carat emerald-cut diamond ring designed by Dallas jeweler Sue Gragg of Sue Gragg Precious Jewels, with experts saying it may have been bigger and more valuable than the one Trump Jr gave Guilfoyle in 2022. 

Don Jr, 47, began dating Anderson in spring 2024 and in September 2024, was caught locking lips with the Florida socialite.

DailyMail.com exclusively obtained photos at the time that showed the two kissing during an intimate date at a Palm Beach restaurant. 

Afterwards, a source said Don Jr.’s dalliance with Bettina was an open secret in the ritzy Florida town, and that they were spotted enjoying each other’s company frequently despite not having publicly split from Guilfoyle.

Don Jr dated Guilfoyle, now the Ambassador to Greece, from 2018 to 2024

It was later divulged by Forbes that Anderson’s ring was an eight-carat emerald-cut diamond ring designed by Dallas jeweler Sue Gragg of Sue Gragg Precious Jewels, with experts saying it may have been bigger and more valuable than the one Trump Jr gave Guilfoyle in 2022

Then, in early December 2024, Don Jr. and Bettina were spotted enjoying a romantic night out together.

The pair have appeared at high profile events, including the president’s trip to the Super Bowl in New Orleans and Trump’s March address to Congress, throughout 2025.

Sources told The Daily Mail that many began speculating wedding bells were near when Anderson took center stage at an official dinner held in honor of Saudi Arabia last month.

MAGA insiders told the Daily Mail that Anderson’s appearance in a dazzling Safiyaa teal caped gown set tongues wagging.

‘Don is in love with Bettina,’ one insider said, ‘He is telling friends “This is the woman I love.”

‘His dad loves her. They all feel she is classy and has an impeccable fashion sense.

‘Don brought her to the most high profile White House gala so proudly.’

Anderson was photographed with Don Jr’s half-sister Tiffany Trump, 32, and her husband Michael Boulos, 28. 

Guilfoyle has not yet publicly commented on her ex’s engagement

Tiffany and Michael married in 2022 at her father’s Mar-a-Lago estate. 

Her presence at the dinner, which was also attended by First Lady Melania Trump, 55, indicates just how quickly Anderson has become part of the Trump inner circle.

Anderson was born into one of Palm Beach’s old-money banking families, the daughter of Palm Beach society couple Harry Loy Anderson Jr, a banker, and his wife Inger, an immigrant from Sweden.

Best known as H. Loy, the elder Anderson became president of a small bank, Worth Avenue National Bank, in 1970 then went on to take over a slew of other financial institutions.

Don Jr was married to first wife Vanessa from 2005 to 2018 and they have five children.

The pair appear to still be on good terms, as Vanessa attended a reception at the White House Sunday evening and was shouted out by President Trump. 

He dated Guilfoyle from 2018 to 2024.