The Shocking Split: What Really Happened Between Don Jr. And Kimberly Guilfoyle And Their New Life-Altering Engagements

The political power couple known as "Don Jr. and Kim" has officially parted ways, a stunning development that has reshaped the landscape of one of America's most prominent political families. As of December 2025, the long-term engagement between Donald Trump Jr. and Kimberly Guilfoyle is over, a split that was followed by a whirlwind of personal and professional changes for both high-profile figures. The news of their separation, which quietly took place in late 2024, has been overshadowed by even more recent, headline-grabbing announcements, including a new engagement for Don Jr. and a major international move for Guilfoyle. The end of their six-year romance, which began in 2018 and led to an engagement in 2021, marks the conclusion of a significant chapter in Republican politics and fundraising. Both have since embarked on dramatically different paths, with one finding new love and the other pursuing a new diplomatic and media career abroad, making this a story of two entirely new beginnings.

Complete Biography and Relationship Timeline

The relationship between Donald Trump Jr. and Kimberly Guilfoyle was a political and media spectacle from the start, uniting two powerful figures with deep ties to the Republican establishment. Their romance began shortly after Don Jr. filed for divorce from his first wife, Vanessa Trump, and quickly became a fixture at high-profile political rallies and fundraising events.

Donald John Trump Jr. Profile

• Born: December 31, 1977, in New York City, New York.
• Parents: Donald J. Trump and Ivana Trump.
• Education: B.S. in Economics from the Wharton School at the University of Pennsylvania.
• Career: Executive Vice President of The Trump Organization, political activist, and author.
• First Marriage: Vanessa Haydon (2005–2018).
• Children: Five children with Vanessa Trump.

Kimberly Ann Guilfoyle Profile

• Born: March 9, 1969.
• Education: J.D. from the University of San Francisco School of Law.
• Career: Former prosecutor, political analyst, journalist, and television news personality.
• Previous Roles: Co-hosted *The Five* on Fox News (2006–2018), served as the United States Ambassador to Greece.
• First Marriage: Gavin Newsom (2001–2006).
• Second Marriage: Eric Villency (2006–2009).
• Children: One son, Ronan Anthony Villency.

The Don Jr. and Kim Relationship Timeline

The couple’s journey was marked by intense political activism and a high degree of public scrutiny.

• 2018: Romance goes public shortly after Don Jr.'s divorce filing.
• 2020: Don Jr. proposes to Guilfoyle, though the engagement is kept secret for over a year.
• January 2022: The engagement is publicly confirmed.
• Late 2024: The couple quietly separates, ending their engagement.
• Early 2025: Guilfoyle moves to Athens, Greece, to take on a new role.
• December 2025: Don Jr.'s new engagement to Bettina Anderson is announced.

The Shocking Split and Don Jr.'s Whirlwind New Engagement

The dissolution of the engagement between Don Jr. and Guilfoyle was a surprise to many observers, especially given their unified front during various political campaigns and legal challenges. Though the exact reasons for the split remain private, the news became definitive with the emergence of a new woman in Don Jr.'s life.

A New Chapter with Bettina Anderson

Just weeks after the separation became clear, Donald Trump Jr. announced his engagement to model and socialite Bettina Anderson. The announcement was made at a high-profile White House gathering, with President Trump himself delivering the news. Anderson, who has been dating Don Jr. for over a year, is a well-known figure in New York social circles. The speed of the new engagement—coming so soon after the end of his lengthy relationship with Guilfoyle—has ignited significant media discussion. Sources close to the former couple indicated that Kimberly Guilfoyle was "processing" the news of her ex-fiancé's rapid path to a new marriage commitment.

The Lingering Question of Real Estate

A peculiar detail surrounding the split involves the $9.7 million Jupiter, Florida, mansion the former couple purchased together in 2021. As of the latest reports, Don Jr. still reportedly co-owns the property with his ex-fiancée, Guilfoyle, a complex financial entanglement that remains unresolved amidst their separate life transitions. The future of this luxury property, which served as their primary residence, is one of the last remaining public ties between the former power duo.

Kimberly Guilfoyle's New Life and Diplomatic Role in Greece

In a dramatic pivot, Kimberly Guilfoyle has not only ended her engagement but has also made a transatlantic move, relocating to Athens, Greece. This move is tied to a significant new professional and diplomatic role, signaling a major shift away from the day-to-day American political grind.

A New Diplomatic and Media Focus

Guilfoyle’s new position leverages her extensive background in law, media, and politics, now on an international stage. Her move to Greece has been described as a fresh start, allowing her to focus on new global initiatives. She has already begun to integrate into the country's political and social life, making high-level appearances.

Looking for a "New Husband"

Embracing her new independence, Guilfoyle has been outspoken about her personal future. During a recent public appearance in her new home country, she reportedly told the Greek President that she was ready to "get a new husband." This comment highlights her forward-looking attitude and her readiness to fully embrace her new chapter, both professionally and personally, on a different continent. The split between Don Jr. and Kimberly Guilfoyle ultimately served as a catalyst for profound change in both their lives. While Donald Trump Jr. is settling into his new engagement with Bettina Anderson and maintaining his political and business activities in the US, Kimberly Guilfoyle has redefined her career with a prestigious international move. The story of "Don Jr. and Kim" is now a tale of two separate, high-stakes new beginnings.