Ever since Donald Trump Jr. proposed to Bettina Anderson, people have been curious about his ex, Kimberly Guilfoyle’s reaction to the engagement. The former couple was together for six years before calling it quits in 2024.
While sources earlier claimed that Guilfoyle was not very happy with Don Jr. and Anderson’s romance, the 56-year-old diplomat has now broken her silence to clarify her feelings on the matter.
In a recent interview with The New York Times, Guilfoyle said she is happy for her ex and wishes him all the best. She said, “I’m happy for Don. I wish him, of course, all the best.”
🚨 BREAKING: President Trump just announced from the White House that Donald Trump Jr. and Bettina Anderson are officially engaged and planning to get married.
Yes, this was announced at the White House.
America, 2025. pic.twitter.com/ptpOjIRBbu
— Brian Allen (@allenanalysis) December 16, 2025
Reports of Don Jr. and Guilfoyle’s romance first emerged in 2018. The couple got engaged at the end of 2020 but did not announce their engagement until January 2022.
Meanwhile, Guilfoyle helped her would-be in-laws by leading the fundraising division for Donald Trump’s 2020 presidential campaign.
However, the relationship eventually changed, and the pair called it quits in 2024. On Dec. 15, 2025, Trump announced his son’s engagement to Palm Beach socialite Anderson during an event at the White House.
At the time, sources said that although Don Jr. and Guilfoyle ended their relationship amicably, it was still difficult for the latter to see her ex with another woman.
An insider told People, “Kimberly knows Don well, and they’re still great friends, but she has major concerns when it comes to his relationship with Bettina. The engagement was difficult for Kimberly to see, and she felt it only added to her doubts about the relationship.”
Sources also revealed that Don Jr., 48, chose Anderson, 40, in part to impress his father. As a model and socialite, Anderson shares some similarities with Melania Trump, and the president reportedly thinks highly of her.
Moreover, Anderson received a significantly more expensive engagement ring. According to jewelry experts, her band features an 8-carat diamond and is valued between $650,000 and $800,000.
By comparison, Guilfoyle’s engagement ring featured a 5-carat diamond and was priced between $65,000 and $125,000.
Most people forget that @GavinNewsom was married to Donald Trump Jr’s ex @kimguilfoyle. Yes, that Kimberly Guilfoyle.
One of the many things people are going to be reminded of in the months ahead… pic.twitter.com/6BAyN99AhJ
— Don Winslow (@donwinslow) March 20, 2025
Nevertheless, the strain in Guilfoyle’s relationship with the Trumps has not affected her political career. Despite her split with Don Jr., she was appointed the Ambassador to Greece in November 2025.
Also, Don Jr. was not the first political person Guilfoyle got into a relationship with. She was previously married to Democratic Governor of California Gavin Newsom.
As his wife, Guilfoyle served as the First Lady of San Francisco between 2004 and 2006. The couple got married in 2001, but filed for divorce in January 2005, citing long-distance as the reason.
