Vanessa Trump: Vanessa Trump’s past relationships are anything but ordinary—here’s who she dated before Tiger Woods
Vanessa Trump, 47, is reportedly in a secret relationship with golf legend Tiger Woods, 49, according to The Daily Mail. While neither Vanessa nor Tiger has publicly confirmed their romance, sources say they have been quietly dating since Thanksgiving 2024—and if you look closely, the signs were there all along.
For months, Vanessa has been subtly engaging with Tiger’s world on social media. She followed his personal Instagram, his TGR Foundation, the Tiger Woods Center, and even multiple fan pages. As early as December 2024, she was seen liking posts of Woods, including family moments with his kids and a heartfelt tribute he shared for his late mother, Kultida Woods, who passed away in February.
Their relationship, according to Page Six, is still in its early stages, but insiders say it is heading in a serious direction. Vanessa and Tiger live just 20 minutes apart in Florida, and their children even attend the same Palm Beach school. Her eldest daughter, Kai Trump, 17, is an avid golfer who has been seen playing alongside former President Donald Trump—a possible connection point for her mother and Woods.
The pair is reportedly keeping things private for now, choosing to spend quiet nights at Tiger’s Jupiter Island estate rather than making public appearances together.
While this rumored romance is making headlines, it’s far from Vanessa Trump’s first high-profile relationship. Let’s take a look at her dating history before Tiger Woods.
Donald Trump Jr. (2005–2018)
Credit: X/@DonaldJTrumpJr
Vanessa was previously married to Donald Trump Jr., the son of former President Donald Trump. The two tied the knot in 2005 and were together for over a decade before divorcing in 2018. They share five children, including Kai Trump, who has become a rising golf star and social media influencer.
Leonardo DiCaprio (1998–1999)
Credit: X/@LeoDiCaprio
At just 20 years old, Vanessa was linked to Hollywood superstar Leonardo DiCaprio, according to Hello! Magazine. While their romance was never highly publicized, sources at the time claimed the two dated briefly, though it didn’t last long.
Prince Khalid bin Bandar bin Sultan Al Saud (1998–2001)
Vanessa’s most serious relationship before Trump Jr. was with Saudi Prince Khalid bin Bandar bin Sultan Al Saud. According to Page Six, they were deeply in love and even lived together for a few years. The couple planned to marry, but world events changed everything.
When the 9/11 attacks occurred in 2001, the prince abruptly returned to Saudi Arabia, effectively ending their relationship. “They were inseparable,” a source told Page Six.
Valentin Rivera (High School Years)
During her school years, Vanessa had a relationship with Valentin Rivera, who was allegedly affiliated with the Latin Kings gang. According to Page Six, she dated Rivera in high school and even attended prom with him.
