The Three Women: Who Is Don Jr.'s New Wife-to-Be After His Shocking Split?
Donald Trump Jr.’s romantic life has once again dominated headlines, with a whirlwind of high-profile relationships that have captured the public’s attention. As of late 2024 and heading into early 2025, the eldest son of the former President has moved swiftly from a long-term engagement to a new, surprising path to the altar, solidifying a new chapter in his personal story.
The transition follows a major split and an even more rapid engagement, making the current status of "Don Jr.'s wife" a fascinating and constantly evolving topic. The latest news confirms his engagement to Palm Beach socialite and philanthropist, Bettina Anderson, just weeks after his separation from former fiancée Kimberly Guilfoyle was made public.
The Man Behind the Headlines: Donald Trump Jr. Biography
Donald John Trump Jr., often simply known as "Don Jr.," is an American businessman, political activist, and author. He is the eldest child of Donald Trump and his first wife, Ivana Trump.
- Born: December 31, 1977 (New York, New York)
- Parents: Donald Trump and Ivana Trump
- Education: The Buckley School; The Hill School; University of Pennsylvania (B.S. in Economics, Wharton School)
- Career: Executive Vice President of The Trump Organization, political campaigner, author, and media personality.
- Children: Five (with ex-wife Vanessa Trump)
Chapter 1: The Ex-Wife—Vanessa Trump (2005–2018)
Before his highly publicized political relationships, Donald Trump Jr. was married to Vanessa Kay Haydon, a former model and socialite. Their marriage lasted 12 years and produced five children, establishing the foundation of Don Jr.’s family life.
The Marriage and Divorce
Don Jr. and Vanessa met at a fashion show in 2003 and were introduced by Donald Trump Sr. himself. They married in November 2005 at the Mar-a-Lago Club in Palm Beach, Florida, with the ceremony presided over by a family friend, Judge Maryanne Trump Barry, Don Jr.’s aunt.
Over the course of their marriage, they had five children: Kai Madison, Donald John III, Tristan Milos, Spencer Frederick, and Chloe Sophia.
In March 2018, Vanessa filed for divorce. The split was reported to be amicable, with the couple stating they would continue to co-parent their five children. The divorce was finalized in 2018.
Vanessa’s Current Life Update (2025)
In a significant and recent development, Vanessa Trump has also moved on. As of early 2025, reports indicate that she is in a relationship with legendary golfer Tiger Woods. The two have reportedly been quietly dating for some time, a surprising new pairing that has kept Vanessa in the public eye while maintaining a focus on co-parenting with her ex-husband.
Chapter 2: The Ex-Fiancée—Kimberly Guilfoyle (2018–2024)
Following his divorce, Don Jr. began a high-profile relationship with former Fox News host and political advisor Kimberly Guilfoyle. The relationship quickly became a staple of Republican political rallies and events.
The Political Power Couple
Guilfoyle, a former prosecutor and co-host of *The Five*, began dating Don Jr. in 2018. Their relationship was characterized by their joint political activism and prominent roles in the Trump political sphere, including the 2020 and 2024 presidential campaigns.
The couple became engaged in late 2021, though the news was not widely reported until early 2022. They were a fixture in the Palm Beach and political social scenes, often appearing together at Mar-a-Lago and campaign events.
The Late 2024 Separation and New Role
The power couple’s engagement came to an end in late 2024. Reports of their separation surfaced around the time Kimberly Guilfoyle accepted a new role as an Ambassador to Greece in President Trump’s administration. The split, confirmed in the fall of 2024, marked the end of a highly visible partnership.
Chapter 3: The New Fiancée—Bettina Anderson (2025)
The most recent and arguably most surprising development in Don Jr.’s love life is his swift engagement to Bettina Anderson. This news, confirmed by President Donald Trump himself, came just weeks after the Guilfoyle separation, ensuring the story remained at the forefront of the news cycle.
Who is Bettina Anderson?
Bettina Anderson is a Palm Beach-based socialite, philanthropist, and non-profit executive. She is a prominent figure in the Florida social scene, known for her work with various charitable organizations and her background in the arts.
- Background: Anderson is the daughter of entrepreneur Harry Loy Anderson Jr. and philanthropist Inger Anderson.
- Education & Career: She graduated from Columbia University in 2009 with a degree in art history, criticism, and conservation. Her professional background includes work as a model, social media influencer, and the founding of a disaster relief nonprofit.
- Relationship Timeline: Don Jr. and Anderson reportedly began dating in mid-2024, keeping the relationship quiet initially. Their engagement was announced in late 2024/early 2025, just a short period after his split from Guilfoyle.
The Shock Engagement and Future Plans
The news of the engagement to Anderson, who is described as a model and local entrepreneur, was a major revelation for the public. The rapid progression of the relationship, from initial dating to engagement within approximately six months, highlights a significant shift in Don Jr.'s personal life.
While the wedding date for Don Jr. and Bettina Anderson is not yet public, the engagement marks the third major chapter in his adult relationships. The move from a political partnership with Kimberly Guilfoyle to a more society-focused relationship with Bettina Anderson has been viewed by observers as a notable change in his personal priorities, though he remains a dominant figure in the political landscape.
Topical Authority: The Trump Family's Relationship Dynamics
Donald Trump Jr.'s relationships are often viewed through the lens of the broader Trump family dynamic, which is characterized by high-profile marriages, political influence, and media scrutiny. The family's public figures—including Donald Trump Sr., Ivanka Trump, and Eric Trump—have all had their personal lives intensely scrutinized, making Don Jr.'s latest engagement a continuation of this trend. His new fiancée, Bettina Anderson, brings a blend of Palm Beach society and philanthropic background to the family, a contrast to the overtly political nature of his previous engagement to Kimberly Guilfoyle.
The amicable co-parenting relationship he maintains with ex-wife Vanessa Trump, which includes family appearances at major events, speaks to a desire to keep family matters stable despite the changes in his romantic life. The entities involved—from Mar-a-Lago to the political campaign trail—all serve as backdrops to these personal developments, intertwining his private life with his public persona as an executive vice president and political activist.
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