Kimberly Guilfoyle, the 56-year-old U.S. Ambassador to Greece, has reportedly responded with skepticism and frustration to news of her ex-fiancé Donald Trump Jr.’s engagement to Palm Beach socialite Bettina Anderson, 39, according to sources close to the ambassador in Athens, Greece.
Trump Jr., 47, proposed to Anderson at Camp David, Maryland, on December 15, 2025. The engagement was announced during a White House Christmas party on Monday, where 20 close friends had gathered at the White House to celebrate the occasion.
However, sources at the Athens embassy say Guilfoyle has been ill-tempered in recent days following the announcement. “She yells at meetings,” one embassy source said. “She came late to a Christmas party and barely stayed. Not the usual social butterfly that she usually is.”
Guilfoyle has allegedly expressed doubts about the relationship’s longevity, believing Anderson is more interested in the prestige and attention that comes with being connected to the Trump family. Sources say Guilfoyle doesn’t believe the relationship will last and uses a derogatory nickname when referring to Anderson in private conversations.
The ambassador currently serves in her diplomatic post in Athens, but the engagement news appears to have disrupted her typically composed demeanor. Sources describe her as agitated by Anderson and note a marked change in her professional conduct.
Adding complexity to the situation is a financial tie that remains between the former couple. In April 2021, Guilfoyle and Trump Jr. purchased a $10 million mansion together in Jupiter, Florida. The house remains jointly owned, creating an ongoing connection between the ex-fiancés that requires resolution.
Guilfoyle and Trump Jr. began dating in 2018, shortly after his previous marriage ended. The couple got engaged in December 2020, but their engagement ended in 2024. Trump Jr. was previously married to Vanessa Trump and has five children from that marriage.
Anderson is a Palm Beach socialite whose father, Harry Loy Anderson Jr., became the youngest U.S. bank president at age 26. She represents a different social circle from Guilfoyle, with connections to the Florida elite community.
Before her relationship with Trump Jr., Guilfoyle had been married twice. She was married to California Governor Gavin Newsom from 2001 to 2006, and to businessman Eric Villency from 2006 to 2009.
The engagement announcement at the White House marked a significant moment for Trump Jr., who appears to have moved quickly from his previous relationship to his new engagement. The proposal at Camp David took place at the Maryland presidential retreat, a location steeped in American political history.
Guilfoyle’s appointment as U.S. Ambassador to Greece represented a prestigious diplomatic posting following her relationship with Trump Jr. She has been working from Athens, where she manages bilateral relations between the United States and Greece. However, the recent engagement news appears to have affected her professional performance, according to embassy observers.
The jointly owned Florida property continues to be a topic of concern. The property’s joint ownership status means both parties retain legal interests in the real estate, requiring eventual resolution between the former couple.
Sources close to Guilfoyle describe her as questioning whether Anderson is genuinely suited for Trump Jr. or merely attracted to the family name and political connections, according to reports.
The situation highlights the complicated nature of high-profile breakups, particularly when they involve political families and international diplomatic postings. Guilfoyle’s position in Athens places her thousands of miles away from Washington, yet the engagement announcement at the White House Christmas party has clearly affected her emotional state and professional conduct.
Despite the distance between Athens and Washington, sources say Guilfoyle remains well-informed about developments in Trump Jr.’s personal life. Her response to the engagement suggests the relationship’s end may not have been as amicable as previously suggested, with lingering feelings complicating what was meant to be a clean break between the former couple.
The engagement represents Trump Jr.’s third serious commitment, following his marriage to Vanessa Trump and his engagement to Guilfoyle. At 47, he joins his new fiancée in navigating the intense scrutiny that comes with connections to one of America’s most prominent political families.
For Guilfoyle, the news arrives as she establishes herself in her ambassadorial role in Greece. The diplomatic posting requires maintaining composure and professionalism, making her reported outbursts at meetings and abbreviated appearance at a Christmas party notable departures from expected diplomatic protocol.
As both parties move forward with their separate lives—Guilfoyle in her diplomatic capacity in Athens and Trump Jr. planning his wedding to Anderson—the jointly owned Florida property and their shared history remain connecting threads between two people whose relationship ended but whose financial and emotional ties have yet to be fully resolved.
