The Wedding That Never Was: Why Donald Trump Jr. And Kimberly Guilfoyle Called Off Their Engagement
The highly anticipated wedding between Donald Trump Jr. and former Fox News host Kimberly Guilfoyle, a union that would have solidified one of the most powerful couples in conservative politics, will never happen. As of December 22, 2025, the couple has officially separated, and the wedding plans have been permanently called off.
This news comes as a major shock to those who followed their six-year relationship and engagement, which was confirmed in 2021 after a reported proposal in late 2020. The biggest twist? Donald Trump Jr. has already moved on, confirming his engagement to a new partner, Bettina Anderson, just weeks after the split from Guilfoyle was finalized.
The Shocking Split and New Engagement: A Timeline of Events
The relationship between Donald Trump Jr. and Kimberly Guilfoyle was a political power pairing, beginning in 2018 following Don Jr.'s divorce from his ex-wife, Vanessa Trump. Their engagement was a poorly kept secret for some time before being publicly confirmed in 2021.
Despite their high-profile status and the dazzling engagement ring Guilfoyle wore, the couple never set a firm wedding date.
The Canceled Wedding and Late 2024 Separation
Rumors of a breakup began swirling in mid-2024, but the separation was officially confirmed in late 2024. After years of speculation and no wedding date, the political couple quietly ended their engagement, which had lasted approximately four years.
Sources close to the couple confirmed the split was not a sudden event but the culmination of a drifting apart.
The split was notable not just for the end of a prominent relationship, but also because the couple still owned a $9.7 million mansion in Jupiter, Florida, together, raising questions about asset division following the breakup.
Donald Trump Jr.'s Surprise New Fiancée: Bettina Anderson
In a dramatic turn of events that dominated political and social headlines, Donald Trump Jr. announced his engagement to Palm Beach socialite Bettina Anderson in December 2024.
The announcement was made by President Donald Trump himself at the White House, marking an unusually high-profile confirmation for the relationship.
Anderson, known for a relatively lower profile compared to Guilfoyle, is a model and socialite who was first linked to Don Jr. in August 2024, just months before the official engagement announcement.
This swift transition from a long-term, high-profile engagement to a new, rapid engagement has fueled intense media scrutiny and commentary on the Trump family's personal life.
Full Profile: Donald Trump Jr. and Kimberly Guilfoyle
The former couple’s individual careers and backgrounds are critical to understanding their influence in the conservative movement and their relationship dynamics.
Donald John Trump Jr. (Don Jr.)
- Born: December 31, 1977
- Birthplace: New York, New York, U.S.
- Parents: Donald Trump and Ivana Trump
- Key Roles: Executive Vice President of The Trump Organization, Political Activist, Businessman.
- Education: The Wharton School at the University of Pennsylvania.
- Previous Marriage: Vanessa Trump (married 2006, divorced 2018); they share five children.
Kimberly Ann Guilfoyle
- Born: March 9, 1969
- Birthplace: San Francisco, California, U.S.
- Key Roles: Former Prosecutor, Media Personality (Co-host of Fox News' The Five), Senior Advisor for the Trump re-election campaign, and currently serves as the United States ambassador to Greece (since 2025).
- Education: University of California, Davis, and the University of San Francisco School of Law.
- Previous Marriages: Eric Villency and Gavin Newsom (current Governor of California).
The Political and Social Fallout of the Breakup
The relationship between Don Jr. and Guilfoyle was always deeply intertwined with the "Make America Great Again" (MAGA) movement. They were a fixture at rallies, serving as a high-energy, outspoken political duo.
Their split raises questions about the future political dynamics surrounding the Trump family, especially as the 2024 election cycle concluded and focus shifted to future campaigns. Guilfoyle, a former prosecutor and prominent media figure, was a significant political asset to Don Jr.
The breakup also occurred during a period of intense legal and financial scrutiny for the Trump family, including the New York Attorney General’s investigation, which may have added stress to the relationship.
Kimberly Guilfoyle has since taken on a new role as the U.S. Ambassador to Greece, a position that signals a significant shift in her career path away from domestic political campaigning.
The Contrast: Guilfoyle vs. Anderson
The transition from Kimberly Guilfoyle to Bettina Anderson marks a stark contrast in Don Jr.'s public relationships.
- Kimberly Guilfoyle: An established figure in politics and cable news, known for her fiery speeches and deep involvement in the Trump administration's inner circle. She represented a powerful, political partner.
- Bettina Anderson: A Palm Beach socialite with a background in modeling and a more private life, suggesting a potential shift towards a less politically focused personal life for Don Jr.
The speed of the new engagement suggests a desire for a fresh start, moving quickly past the years of an unfulfilled engagement with Guilfoyle. The political world is now waiting to see if Don Jr. and Bettina Anderson will set a wedding date sooner than his previous engagement, and whether this new relationship will be as publicly visible in the political arena as the last.
FAQs: Answering Your Burning Questions About the Non-Wedding
Did Donald Trump Jr. and Kimberly Guilfoyle ever get married?
No, Donald Trump Jr. and Kimberly Guilfoyle never married. They were engaged from late 2020/early 2021 until they separated in late 2024.
Why did Donald Trump Jr. and Kimberly Guilfoyle break up?
While the exact, detailed reasons for the split are private, sources indicated that the couple had grown apart after six years together and a long engagement that never led to a wedding. The separation was reported in late 2024.
Who is Donald Trump Jr. engaged to now?
Donald Trump Jr. is currently engaged to Bettina Anderson, a Palm Beach socialite and model. Their engagement was announced in December 2024.
What is Kimberly Guilfoyle doing now?
Following her separation from Donald Trump Jr., Kimberly Guilfoyle was appointed and is serving as the United States Ambassador to Greece, a significant diplomatic role.
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