ORLANDO, FLORIDA - FEBRUARY 26: Don Trump, Jr. and Kimberly Guilfoyle stand on stage as they address the Conservative Political Action Conference being held in the Hyatt Regency on February 26, 2021 in Orlando, Florida. Begun in 1974, CPAC brings together conservative organizations, activists, and world leaders to discuss issues important to them. (Photo by Joe Raedle/Getty Images)
Donald Trump Jr. and Kimberly Guilfoyle have ended their relationship, insiders revealed to Page Six. Trump Jr., 46, has reportedly moved on with Palm Beach socialite Bettina Anderson, adding fuel to months of speculation about tension between the high-profile couple.
Sources say Trump Jr. and Guilfoyle, 55, have been struggling for over a year. “They haven’t been getting along,” one insider shared. “They bicker in public at Mar-a-Lago—not explosive fights, but you can tell when a couple is arguing.”
While some sources described the relationship as “rocky,” others confirmed the split outright.
Trump Jr. and Anderson were first spotted together in September, appearing cozy at Honor Bar in Palm Beach. The Daily Mail recently captured photos of the pair holding hands after a romantic dinner at Buccan to celebrate Anderson’s 38th birthday.
“Bettina and Don have been together for a few months and are very happy,” a source said. “It’s a natural fit—everyone is thrilled for them.”
The pair have reportedly been spending nights at Anderson’s home and were seen sharing a corner booth at Buccan, holding hands and chatting warmly with other patrons.
Anderson, the daughter of banker Harry Loy Anderson Jr. and a favorite subject of famed photographer Slim Aarons, has long-standing ties to the Trump family. She attended the Republican National Convention in July with Vanessa Trump, Don Jr.’s ex-wife, and was seen chatting with her during the event.
Guilfoyle, a former TV host and prominent Trump supporter, has been a fixture in the Trump family’s public life. However, rumors have persisted that she didn’t quite fit in with the clan.
“The family doesn’t like her,” one source claimed, though others have pushed back. Eric Trump previously said, “I completely disagree with the narrative and happen to think the world of Kimberly.”
Despite the breakup, Guilfoyle and Trump Jr. maintained a strong professional partnership, with joint speaking engagements leading up to the 2024 election.
In the middle of the media turmoil, she was named the new US ambassador to Greece by the Trump transition team. “For many years, Kimberly has been a close friend and ally. Her extensive experience and leadership in law, media, and politics along with her sharp intellect make her supremely qualified to represent the United States, and safeguard its interests abroad,” the statementy read.
While representatives for both Trump Jr. and Guilfoyle declined to comment, the split marks the end of a five-year relationship that included a 2020 engagement.
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