Kimberly Guilfoyle Vows to Stay in Donald Trump Jr.’s Life Despite Split
Donald Trump Jr. and Kimberly Guilfoyle arrive to a press conference on the census by President Trump in the Rose Garden of the White House on July 11, 2019 in Washington, DC. (Cover Image Source: Mark Wilson/Getty Images)
Kimberly Guilfoyle, 55, is determined to maintain her presence in Donald Trump Jr.’s life, despite their recent breakup and his new relationship with Florida socialite Bettina Anderson. Guilfoyle and Trump Jr., who dated from 2018 to 2024 and were engaged for four years, officially ended their relationship in December 2024.
However, insiders reveal that Guilfoyle feels her connection to the former president’s eldest son is unbreakable due to their shared history and mutual circles. “She feels like they’ll always have a connection,” a source told Page Six. “Kimberly and Don Jr. have many mutual friends and run in the same circles, so they’ll continuously cross paths throughout their lives.”
The pair have already proven this to be true, attending multiple events together during President Donald Trump’s second inauguration. At a candlelight dinner on January 19 and the Hispanic Inaugural Ball, Guilfoyle and Trump Jr. were seen standing alongside each other without any apparent tension.
Despite the presence of Anderson, who attended the candlelight dinner with Trump Jr., sources say Guilfoyle remained unfazed. “She didn’t feel awkward at all spending time with Don Jr. during the inauguration or any of the parties or events leading up to it,” an insider shared.
“Don feels the same way. He still has a great relationship with Kimberly, and there’s been zero awkwardness whenever they interact since their split.” Guilfoyle’s new role as the U.S. Ambassador to Greece, a position she was offered under President Trump’s administration, hasn’t altered her determination to remain close to the Trump family.
“Although Kim is serving as ambassador to Greece, she’s not going anywhere in terms of fading out of the public eye,” said the source. “She’s also very close with the Trump family and will remain in contact with President Trump about her new role.”
Meanwhile, Donald Trump Jr., 47, and Anderson, 38, have been moving forward with their relationship, with reports suggesting Trump Jr. is essentially living at Anderson’s townhouse in Palm Beach. Anderson first appeared in the Trump family’s orbit at the Republican National Convention in July 2024, seated near Trump Jr. and Guilfoyle.
Despite their breakup, Guilfoyle and Trump Jr. continue to navigate their overlapping lives, maintaining cordial relations as they move forward in separate directions.
