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Vanessa Trump, former wife of Donald Trump Jr., has been living a life full of romance. Her recent romantic affair with Golf legend Tiger Woods has made headlines in the top news portals. While the development has piqued public interest, it has led many to dig deeper into her past dating history.
Vanessa Trump’s romantic life is filled with escapades ranging from the President’s son to a Hollywood celebrity to a Saudi Prince. Her recent entanglement with Tiger Woods has been confirmed with a social media post by the legendary golfer. Want to dive into the dating history of Vanessa Trump? Read on.
Hollywood fling with Leonardo DiCaprio
During her teenage days, Vanessa Trump embarked on a modelling career which led her to her intriguing dating history, including high-profile figures. In the late 1990s, Vanessa Trump was romantically linked with Hollywood heartthrob Leonardo DiCaprio.
Their brief relationship caught media attention, highlighting her ties to the entertainment industry. Though there are hardly any details about their brief affair, this relationship marked her publicized romantic endeavors (via Hello Magazine).
A royal affair with Prince Khalid bin Bandar bin Sultan Al Saud
Vanessa Trump was also linked with Saudi Prince Khalid bin Bandar bin Sultan Al Saud. They dated for three years, between 1998 to 2001. After the 9/11 attack, the relationship ended abruptly after Prince Khalid left the country surrounding his father’s alleged ties to Al-Qaeda.
According to a report by Page Six, she wanted to marry the prince before the world events got in the way. A source told Page Six, “They dated from 1998 to 2001 and lived together. He ditched her on 9/11; days after, he flew back to Saudi Arabia. They were planning to marry [at the time]. They were inseparable.”
The anonymous source also informed that they were almost inseparable. Later, Prince Khalid married British aristocrat Lucy Caroline Cuthbert, the niece of the Duke of Northumberland, in 2011.
Marriage to Donald Trump Jr.
Vanessa Trump married Donald Trump Jr. in 2005 at Mar-a-Lago in Palm Beach, Florida. The couple met at a fashion show in the early 2000s and then married, which lasted for 13 years. During the marriage, they had five children and it placed Vanessa Trump in the national spotlight as part of America’s first family (via Us Weekly).
Despite their divorce in 2018, they share a collaborative relationship for the sake of their children. According to a report by People, Donald Trump Jr. is ‘cool’ with Vanessa Trump’s relationship with Tiger Woods.
As of early 2025, Vanessa Trump’s personal life has taken a new turn with her relationship with Tiger Woods. The couple, both residents of Florida, have been spotted together at various events, sparking discussions about their romance.
While they kept their relationship relatively private, a recent social media post by Tiger Woods has confirmed their relationship. They have connected over their passion for their respective kids’ golf careers.
This post belongs to FandomWire and first appeared on FandomWire
