5 Shocking Reasons Donald Trump Jr. And Kimberly Guilfoyle’s Engagement Ended And Who He Is Dating Now

The political power couple is no more. As of late 2024 and early 2025, the highly-publicized engagement between Donald Trump Jr. and former Fox News host Kimberly Guilfoyle has reportedly been called off, marking a dramatic end to a relationship that spanned over six years and was a fixture on the American political scene. The news has sent shockwaves through Washington and Palm Beach society, especially as details emerge about Don Jr.’s rumored new partner and Guilfoyle’s surprising new diplomatic role. The couple, who first started dating in 2018 and became engaged on New Year's Eve 2020, had been planning a wedding for years. However, recent reports confirm the end of their relationship, with both individuals moving in new directions. This article breaks down the final chapter of their romance, the reasons behind the split, and the new faces in their lives, providing the freshest, most current information available today, December 12, 2025.

Comprehensive Biographical Profiles: Donald Trump Jr. and Kimberly Guilfoyle

To fully understand the context of their high-profile split, it is essential to look at the professional and personal backgrounds of both Donald Trump Jr. and Kimberly Guilfoyle. Both are established figures with significant careers in business, media, and politics.

Donald John Trump Jr.

• Born: December 31, 1977 (Age 47 as of late 2025)
• Place of Birth: New York City, New York
• Parents: Donald J. Trump and Ivana Trump (Eldest child)
• Education: The Wharton School at the University of Pennsylvania
• Primary Role: Executive Vice President of The Trump Organization, political activist, and author.
• Previous Marriage: Vanessa Haydon (2006–2018), with whom he has five children.
• Current Status: Reportedly dating Palm Beach socialite Bettina Anderson.

Kimberly Ann Guilfoyle

• Born: March 9, 1969 (Age 56 as of late 2025)
• Place of Birth: San Francisco, California
• Descent: Irish and Puerto Rican heritage.
• Education: University of California, Davis, and University of San Francisco School of Law.
• Career Highlights: Former prosecuting attorney in San Francisco and Los Angeles, co-host of Fox News' *The Five* (2006–2018), and national chair of the Trump Victory Finance Committee.
• Previous Marriages: Gavin Newsom (2001–2006) and Eric Villency (2006–2009), with whom she has one son.
• Current Status: Serving as the United States Ambassador to Greece since 2025, following her separation from Don Jr..

The End of the Engagement: What Really Happened to the Wedding Plans?

The engagement between Donald Trump Jr. and Kimberly Guilfoyle, which was first reported in early 2022, was a major story. The couple had been living together in a $9.7 million home in Jupiter, Florida, and were a constant presence at political rallies and events. Despite the long engagement, a wedding date was never formally announced, and rumors of strain began to surface well before the official reports of their separation in late 2024.

1. The Weight of Political and Public Scrutiny

The relationship was one of the most visible in conservative politics, constantly under the media microscope. Both individuals held prominent roles in the political sphere, which subjected their every move and public appearance to intense scrutiny. This pressure cooker environment, especially during a high-stakes political cycle, is often cited as a major factor in the breakdown of high-profile relationships. The couple's joint political activities, while initially bonding, may have ultimately contributed to their personal strain.

2. The Emergence of Cheating Rumors

Before the split was confirmed, there were persistent rumors of tension and infidelity within the relationship. While neither party publicly confirmed the nature of the split, sources close to the couple hinted at mounting tension and "cheating rumors" that devastated Guilfoyle and led to a breaking point in their romance. These unconfirmed reports began circulating just as Don Jr. was spotted with a new companion.

3. Diverging Career Paths: The Diplomatic Shift

A significant and concrete factor is Kimberly Guilfoyle's new career direction. In a move that signaled a major change in her life, Guilfoyle was appointed as the United States Ambassador to Greece in 2025. This demanding diplomatic post requires a full-time commitment and a move overseas, creating an insurmountable geographical and professional distance from Don Jr., who remains focused on the family business and political activism in the United States. This new role effectively formalized the separation.

4. The New Woman: Bettina Anderson

The most compelling evidence of the split was Donald Trump Jr.'s quick progression to a new relationship. Reports surfaced in late 2024 that Don Jr. had moved on with Bettina Anderson, a well-known Palm Beach socialite. The speed with which he was seen with a new partner suggested the end of the engagement was a definitive and possibly unilateral decision. Anderson and Don Jr. have since been photographed together at various events, including a lavish Indian billionaire wedding and family gatherings, cementing her status as his new companion.

5. The Long-Overdue Commitment

The length of the engagement itself became a source of speculation. After getting engaged on New Year’s Eve 2020 and going public with the news in 2022, the lack of a set wedding date led many to believe the couple was hesitant about taking the final step. The four-year gap between the proposal and the split suggested that the relationship may have plateaued, and the long-awaited marriage was simply never going to materialize.

Who Is Bettina Anderson? Don Jr.'s New Companion

The focus has swiftly shifted from the broken engagement to Don Jr.'s new flame, Bettina Anderson. Anderson is an established figure in the affluent Palm Beach, Florida, social circuit, known for her involvement in high-society events and philanthropy.

A New Chapter in Palm Beach

Bettina Anderson is reportedly around 38 years old and has been a familiar face in Florida society for years. She is not a political figure in the same way Guilfoyle was, but she is well-connected and moves in the same elite circles as the Trump family. Her background as a socialite and her presence at presidential-related events with Don Jr. indicate a serious new relationship. The pairing suggests a shift in Don Jr.'s personal life, moving away from the intensely political partnership with Kimberly Guilfoyle to a more traditional social pairing within the Palm Beach elite. While Guilfoyle is now focused on her role as US Ambassador to Greece, Don Jr. and Anderson are reportedly enjoying their time together, signaling a definitive new chapter for both of the former fiancés.