The Unfolding Truth: Is Kimberly Guilfoyle Still With Donald Trump Jr.?

Joe Willms 07 Jul 2025

**The political and social spheres are often rife with speculation, especially when it comes to the personal lives of prominent figures. Few relationships have garnered as much public scrutiny and fascination as that of Donald Trump Jr. and Kimberly Guilfoyle. For years, their partnership was a highly visible component of the Trump political machine, but recent developments have cast a long shadow over their future together, leading many to ask: is Kimberly Guilfoyle still with Donald Trump Jr.?** The answer, as recent reports and confirmations suggest, is a resounding no. What began as a high-profile romance, marked by shared political fervor and public appearances, has seemingly come to an end, leaving behind a trail of rumors, confirmations, and lingering questions about the nature of their split. This article delves into the intricate details of their relationship's evolution, from its public inception to its quiet conclusion, drawing on various reports to piece together the narrative of one of Washington D.C.'s most talked-about couples. ## Table of Contents * [1. The Public Figures: A Glimpse into Their Backgrounds](#the-public-figures-a-glimpse-into-their-backgrounds) * [1.1. Kimberly Guilfoyle: A Path Through Law and Media](#kimberly-guilfoyle-a-path-through-law-and-media) * [1.2. Donald Trump Jr.: Stepping into the Political Limelight](#donald-trump-jr-stepping-into-the-political-limelight) * [2. The Genesis of a High-Profile Romance](#the-genesis-of-a-high-profile-romance) * [3. The Engagement: A Secret Unveiled](#the-engagement-a-secret-unveiled) * [4. Whispers of Trouble: Cracks in the Façade](#whispers-of-trouble-cracks-in-the-facade) * [4.1. Navigating Public Scrutiny and Rumors](#navigating-public-scrutiny-and-rumors) * [5. The Breaking Point: Reports of a Split](#the-breaking-point-reports-of-a-split) * [6. The Bettina Anderson Sighting: A New Chapter for Don Jr.?](#the-bettina-anderson-sighting-a-new-chapter-for-don-jr) * [7. Don Jr.'s Silence Broken: Confirming the Amicable Split](#don-jrs-silence-broken-confirming-the-amicable-split) * [8. Kimberly Guilfoyle's Perspective: Blindsided and Intent on Connection](#kimberly-guilfoyles-perspective-blindsided-and-intent-on-connection) * [9. The Aftermath: Absence from Family Events and Lingering Questions](#the-aftermath-absence-from-family-events-and-lingering-questions) * [10. Conclusion: The End of an Era](#conclusion-the-end-of-an-era) --- ## 1. The Public Figures: A Glimpse into Their Backgrounds Before delving into the intricacies of their relationship, it's essential to understand the individual paths that brought Kimberly Guilfoyle and Donald Trump Jr. into the public eye, shaping their respective personas and the dynamics of their partnership. ### 1.1. Kimberly Guilfoyle: A Path Through Law and Media Kimberly Guilfoyle, born March 9, 1969, has had a multifaceted career that spans law, media, and politics. Her journey began in the legal field, where she served as a prosecutor in San Francisco and Los Angeles. This experience honed her sharp intellect and public speaking skills, which would later become hallmarks of her media career. She transitioned into television news, becoming a prominent personality on various networks, most notably Fox News. Her role as a co-host and analyst on shows like "The Five" solidified her presence in conservative media circles, establishing her as a recognizable face and voice. Beyond her professional achievements, Kimberly Guilfoyle has been married twice, a detail that, alongside her lengthy engagement to Donald Trump Jr., adds a layer of complexity to her romantic history as noted by various publications. Her background as an advisor further illustrates her deep involvement in political and public affairs. | Attribute | Details | | :----------------- | :------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | **Full Name** | Kimberly Ann Guilfoyle | | **Born** | March 9, 1969 | | **Age** | 55 (as of 2024) | | **Nationality** | American | | **Occupation** | Television News Personality, Former Prosecutor, Political Advisor | | **Notable Roles** | Fox News Host, Prosecutor in San Francisco & Los Angeles | | **Marital History**| Married twice prior to engagement with Donald Trump Jr. | ### 1.2. Donald Trump Jr.: Stepping into the Political Limelight Donald Trump Jr., the eldest son of former President Donald Trump and the late Ivana Trump, has carved out his own distinct identity, particularly in the political arena. Initially known for his role in the Trump Organization, his public profile significantly expanded with his father's entry into politics. He became a fervent supporter and surrogate for his father's campaigns, known for his outspoken nature and direct communication style, especially on social media. His political activism and strong conservative views have made him a prominent figure in the Republican party, often appearing at rallies and events, much like his former fiancée. Donald Trump Jr.'s journey from a businessman to a key political voice has been closely watched, and his personal relationships, including the one with Kimberly Guilfoyle, have frequently been subjects of public discourse. | Attribute | Details | | :----------------- | :------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | **Full Name** | Donald John Trump Jr. | | **Born** | December 31, 1977 | | **Age** | 46 (as of 2024) | | **Nationality** | American | | **Occupation** | Businessman, Political Activist, Author | | **Notable Roles** | Executive Vice President of The Trump Organization, Political Surrogate for Donald Trump | | **Family** | Eldest son of Donald Trump and Ivana Trump | ## 2. The Genesis of a High-Profile Romance The relationship between Donald Trump Jr. and Kimberly Guilfoyle went public in 2018, following Don Jr.'s divorce from his first wife, Vanessa Trump. Their coupling immediately captured media attention, given their high profiles and shared political alignment. They quickly became a fixture at Trump rallies, political events, and social gatherings, often appearing side-by-side, projecting an image of unity and strength. Their public displays of affection and mutual support became a notable part of the Trump political narrative, signaling a strong and committed partnership. The question of "is Kimberly Guilfoyle still with Donald Trump Jr." would not have even been conceived during these early, seemingly idyllic days. ## 3. The Engagement: A Secret Unveiled In a surprising revelation, it later emerged that Donald Trump Jr. and Kimberly Guilfoyle had reportedly gotten engaged in 2020. According to the Daily Mail, Don Jr. gave Kimberly Guilfoyle an engagement ring that year, but the couple chose to hide their happy news for two whole years. Keeping such a significant secret for so long added an intriguing layer to their relationship, sparking questions about their desire for privacy versus their highly public personas. This engagement was followed by another significant step in their shared life: the purchase of a $9.7 million Florida mansion in 2021. This move seemed to solidify their commitment, not just to each other, but also to a future together in a state that had become central to the Trump family's post-presidency life. For many, these actions painted a picture of a couple deeply intertwined, making the recent news of their separation even more unexpected. ## 4. Whispers of Trouble: Cracks in the Façade Despite the outward appearance of a strong bond, whispers about the stability of their relationship began to circulate. Reports suggested that Donald Trump Jr. and Kimberly Guilfoyle's relationship had reportedly been "on the rocks lately." These rumors occasionally surfaced, hinting at underlying tensions that were not always visible to the public. One particular incident that fueled speculation occurred during Donald Trump Sr.'s victory speech, where Don Jr. seemed to ignore his fiancée, Kimberly Guilfoyle, on stage, keeping his back to her the whole time. Such public displays, or lack thereof, of affection and acknowledgement, raised eyebrows and contributed to the growing questions about the true state of their relationship. While they might have been stepping out together, some observers noted "more red flags in Donald Trump Jr. and Kimberly Guilfoyle's relationship than red hats at a Trump rally," suggesting that the cracks were more evident to those paying close attention. ### 4.1. Navigating Public Scrutiny and Rumors The couple often found themselves in the crosshairs of public scrutiny, with every interaction analyzed. At times, they attempted to squash breakup rumors. For instance, with election day around the corner, Kimberly Guilfoyle was once again seen attempting to quell speculation about a split with Donald Trump Jr., though reports suggested it "totally backfired." This constant need to address or deflect rumors highlighted the pressure on their relationship. Despite reports that Don Trump Jr. was "fooling around on his longtime fiancée Kimberly Guilfoyle," some sources maintained that "the couple are just fine," indicating a mixed bag of information and an effort to control the narrative. ## 5. The Breaking Point: Reports of a Split The speculation reached a crescendo in December when Page Six broke the news: Guilfoyle and Don Jr., who started dating in 2018, had parted ways after nearly seven years together and four years engaged. This report marked the definitive answer to the question "is Kimberly Guilfoyle still with Donald Trump Jr.?" The news sent ripples through political and social circles, confirming what many had suspected but few had definitively known. The timeline suggests that the split occurred sometime in 2024, based on a series of pictures that surfaced, further solidifying the reports. The formal announcement, or rather, the public confirmation through reputable media outlets, brought an end to months, if not years, of speculation about their future. ## 6. The Bettina Anderson Sighting: A New Chapter for Don Jr.? In the days after the news of their breakup, Donald Trump Jr. was seen holding hands with Florida socialite Bettina Anderson. This sighting, which occurred Monday night in Palm Beach, Florida, amidst questions about his relationship with his fiancée, provided a visual confirmation of his new romantic interests and underscored the finality of his split from Kimberly Guilfoyle. People magazine learned that he and fiancée Kimberly Guilfoyle had indeed broken up in the days after he was spotted holding hands with Bettina Anderson. This public display with a new partner served as a clear indicator that Don Jr. was moving on, further emphasizing that the answer to "is Kimberly Guilfoyle still with Donald Trump Jr." was now unequivocally no. ## 7. Don Jr.'s Silence Broken: Confirming the Amicable Split Following the widespread reports and the public sighting with Bettina Anderson, Donald Trump Jr. broke his silence. He made his first statements since his breakup with Kimberly Guilfoyle, addressing his relationship with her directly. The eldest son of Donald Trump confirmed the news of their rupture, revealing that the split was amicable. In his statement, Don Jr. emphasized, "Kimberly and I will never stop caring for each other and will always keep a special bond." This public declaration aimed to frame the separation as a respectful and mutual decision, despite earlier rumors that the split "may have been messier than it seems." Despite their efforts to appear civil, the couple had been rumored to be navigating a more complex parting behind the scenes. However, Don Jr.'s statement sought to project an image of a clean, amicable break. ## 8. Kimberly Guilfoyle's Perspective: Blindsided and Intent on Connection While Don Jr. presented the split as amicable, reports from Kimberly Guilfoyle's side painted a slightly different picture. Insiders revealed that Kimberly Guilfoyle was "blindsided" by Donald Trump Jr.'s "dalliance" with the Palm Beach socialite, Bettina Anderson. This suggests that the timing or public nature of Don Jr.'s new relationship may have caught her off guard, despite any prior discussions about their breakup. Despite the separation and the emergence of Don Jr.'s new relationship, Kimberly Guilfoyle has reportedly remained intent on keeping a connection with him. An insider exclusively told Page Six that "Kimberly Guilfoyle has every intention of maintaining a relationship with [Donald Trump Jr.]." This desire for continued connection, even after a breakup, highlights the deep ties they forged over nearly seven years together. It suggests that while the romantic chapter may have closed, Kimberly hopes to preserve some form of bond with Don Jr. and, by extension, the Trump family. ## 9. The Aftermath: Absence from Family Events and Lingering Questions The true impact of the breakup on Kimberly Guilfoyle's relationship with the broader Trump family has also become a point of discussion. After splitting from Donald Trump Jr., Kimberly Guilfoyle reportedly isn't invited to Trump family events anymore. Her absence from Don Jr.'s side during a recent family moment with Donald Trump senior further fueled the rumors of their separation and underscored her diminished role within the family's inner circle. Despite this, her social media posts sometimes suggest she wishes she was still included, indicating a lingering attachment or a desire to maintain her connection to the influential family. This situation adds another layer to the complex question of "is Kimberly Guilfoyle still with Donald Trump Jr.?" – not just romantically, but in terms of her proximity and association with the powerful political dynasty. The public narrative continues to unfold, with each new development offering more insight into the private lives of these public figures. ## 10. Conclusion: The End of an Era The journey of Donald Trump Jr. and Kimberly Guilfoyle, from their public debut as a power couple in 2018 to their confirmed separation in late 2023/early 2024, marks the end of a significant chapter in the political and social landscape. The answer to "is Kimberly Guilfoyle still with Donald Trump Jr." is now clear: their romantic engagement has concluded. While Don Jr. has publicly stated the split was amicable and that they will always share a special bond, reports from Kimberly Guilfoyle's side suggest a more complex emotional aftermath, including feeling blindsided by his new public relationship. Her continued desire to maintain a connection, despite her exclusion from Trump family events, speaks volumes about the depth of their long-standing relationship. This high-profile breakup serves as a reminder of the intense scrutiny public figures face and the often-unseen complexities behind their polished public images. What are your thoughts on this high-profile separation? Share your perspectives in the comments below, or explore our other articles on the evolving dynamics of political figures and their relationships.