Donald Trump Jr.'s Enduring Public Romances: From Vanessa Trump to Kimberly Guilfoyle and His New Chapter with Bettina Anderson

Donald Trump Jr., the eldest son of former President Donald Trump, has navigated a high-profile personal life alongside his prominent business and political career. His romantic journey has unfolded largely in the public eye, marked by a lengthy marriage, a significant engagement, and more recently, a new relationship, each chapter reflecting his evolving public persona.

His most substantial relationship began in the early 2000s with Vanessa Haydon, a former model and socialite. They were reportedly introduced by his father, Donald Trump Sr., at a fashion event. Their romance blossomed, leading to their marriage on November 12, 2005, at the lavish Mar-a-Lago estate in Palm Beach, Florida.

During their marriage, Donald Jr. and Vanessa built a large family, welcoming five children: Kai Madison (born May 2007), Donald John III (born February 2009), Tristan Milos (born October 2011), Spencer Frederick (born October 2012), and Chloe Sophia (born June 2014). Their family life was often featured in public appearances, projecting an image of stability and traditional values.

After over a decade of marriage, the couple announced their separation on March 15, 2018, with Vanessa filing for divorce in Manhattan. While no specific reasons were publicly disclosed, the couple released a joint statement: > "We have decided to go our separate ways. We will always have tremendous respect for each other and our families. We have five beautiful children together and they remain our top priority." Their divorce was finalized by the end of 2018 or early 2019. Reports suggested various factors, including the pressures of his father's presidency and unconfirmed rumors of infidelity.

Amidst his marriage to Vanessa, reports from sources like Who's Dated Who suggest Donald Trump Jr. had a brief relationship with singer Aubrey O'Day from August 2011 to March 2012. This alleged affair, which surfaced publicly later, added another layer to the narrative of his personal life, though it was never officially confirmed by either party.

Shortly after his divorce from Vanessa was finalized, Donald Trump Jr. began a highly publicized relationship with Kimberly Guilfoyle in May 2018. Guilfoyle, a former Fox News host and prosecutor, quickly became a prominent figure by his side, particularly within conservative political circles. Their relationship was often described as a power couple within the MAGA movement.

Their engagement was reportedly a quiet affair, occurring on December 31, 2020, on Donald Jr.'s 43rd birthday, but the news was not made public until January 2022. They purchased a home together in Jupiter, Florida, in 2021, signaling a serious commitment. Guilfoyle became an active and vocal supporter in his father's political campaigns, often appearing alongside Donald Jr. at rallies and events.

The relationship with Kimberly Guilfoyle spanned approximately six years, from 2018 to 2024. However, in late 2024, reports began to circulate that their engagement had been called off. While neither party directly confirmed the split, sources close to the couple indicated they had gone their separate ways. Donald Jr. stated to Page Six that he and Guilfoyle would > "never stop caring for each other and will always keep a special bond."

Following the reported end of his engagement to Kimberly Guilfoyle, Donald Trump Jr. was linked to Bettina Anderson, a Palm Beach socialite and model. Their relationship garnered public attention in September 2024 when they were photographed together. They made their public debut as a couple in January 2025, attending several inauguration events for his father.

Bettina Anderson has since been seen accompanying Donald Jr. at various high-profile events, including the Super Bowl and other political gatherings, solidifying their status as a couple. Their relationship marks a new chapter in Donald Trump Jr.'s romantic history, continuing his pattern of public partnerships that often intertwine with his family's political and business endeavors. His relationships have consistently been a subject of public interest, reflecting his prominent position in American media and politics.