‘Will He Behave This Time?’: Tiger Woods Said to Be Secretly Dating Donald Trump Jr.’s ExWife and Things are Heating Up
Mar 14, 2025
Golf legend Tiger Woods has reportedly found new love in an unexpected place — Vanessa Trump, the ex-wife of Donald Trump Jr., according to multiple reports citing sources familiar with the relationship.
The 49-year-old golf icon and the 47-year-old former Trump family member have been quietly
seeing each other since November, creating what insiders are calling “golf’s new power couple” in the wealthy Palm Beach, Florida, enclave where they both reside.
“Tiger and Vanessa have been seeing each other since just before Thanksgiving,” a purported source close to the couple told the Daily Mail. “She comes to his place on Jupiter Island. They’re not living together. She comes over maybe a few nights a week.”
The budding romance has been kept largely under wraps, with the pair avoiding public appearances together.
Tiger Woods is rumored to be dating Vanessa Trump, President Donald Trump’s former daughter-in-law.
(Photos: Grant Lamos IV/Getty Images; REUTERS/Aaron Josefczyk UNITED STATES SPORT GOLF)
“They just love hanging out, having dinner, and schmoozing together. They’re sticking close to home, have decided not to make it a thing and go out in public. Not just yet anyway,” the purported insider added.
Their connection appears to have been strengthened through their children, who attend the same elite private school. Vanessa’s eldest daughter Kai, 17, and Woods’s children Charlie, 16, and Sam, 17, all attend the $38,595-a-year The Benjamin School.
Both Kai Trump and Charlie Woods are aspiring golfers with professional ambitions.
The New York Post reported it was told by its source that the relationship began as a friendship but has since evolved. “But it’s not too serious, it’s heading in that direction, though,” the source said. “They have a lot in common. They’ve both gotten used to public scrutiny. They both know how to keep their private life private. They’re both parents.”
The Post’s source added that while the couple is taking things slow, the relationship has the potential for longevity.
“They’re taking it slow, but I could see this becoming something really serious and permanent,” the unnamed mouthpiece said. “She’s not starstruck by him — she’d date him even if he weren’t famous. Fame doesn’t interest her; that’s what he likes best about her.”
Tiger Woods and Vanessa Trump are secretly datingWoods, 49, and Vanessa Trump. 47, who both live in Florida, have been together since Thanksgiving and are quickly becoming golf's new power couple. Four sources confirmed to SWR that the pair are an item.They live 20 minutes… pic.twitter.com/ILAjP7ceFI— News News News (@NewsNew97351204) March 13, 2025
Geographic proximity likely has played a role in the relationship’s development.
Vanessa lives just 20 minutes from Woods in the affluent Palm Beach area, not far from her ex-husband’s $14 million waterfront mansion in Jupiter’s exclusive Admirals Cove community.
Donald Trump Jr. purchased the sprawling 11,300-square-foot property in 2021 with his then-fiancée Kimberly Guilfoyle. Located just 20 miles from Mar-a-Lago, the luxury home features seven bedrooms, 12 bathrooms, a private dock, a wine room, a theater, and an elevator. The adjacency offered convenience to both his father and his five children with Vanessa.
Vanessa filed for an uncontested divorce from Don Jr. on March 15, 2018, in New York. Since then, she has maintained a relatively low profile romantically. Meanwhile, Don Jr. has recently ended his relationship with Guilfoyle, whom President Trump appointed ambassador to Greece, and has begun dating West Palm Beach socialite Bettina Anderson.
Sources say that Don Jr. and Anderson are aware of Vanessa’s relationship with Woods, which may have eased tensions between Anderson and Vanessa, who were once friends before Anderson began dating Vanessa’s ex-husband.
The news of the relationship has sparked a wave of reactions with the Daily Mail’s readers, with many quick to comment on this unexpected pairing.
“Kai is probably getting the most awesome instruction now. Maybe we’ll see her join the pro circuit soon. I hope she finishes college first though, all of the Trump kids are very well-educated and hopefully the grandkids will be too,” one person commented.
Another noted Woods’ apparent preference in partners and his history of cheating.
“She’s similar looking to Elin, his first wife, but whatever, everyone deserves happiness so I hope this time Tiger won’t stray or he’ll get whacked by another golf club again,” one wrote.
Some commenters took a more comedic approach, with one quipping, “Lots of people are saying F Trump, but Tiger literally is!” while another joked, “Vanessa and Kai have a new daddy.”
“Man, Tiger is down bad. Of all the women in the world, he had to bring potential drama into his life?” questioned one commenter, while another simply stated, “Tiger you old dog.”
More critical voices emerged as well, with one person writing, “She must have a thing for slimeballs that treat women poorly,” and another adding, “Just another addition to Tiger’s harem.”
Others expressed skepticism about the relationship’s future, with one commenting, “Let’s see how long Tiger will behave – neither Vanessa nor her security detail will put up with what his previous ladies have tolerated.”
The relationship news comes at a challenging time for Woods professionally, as he recently ruptured his Achilles tendon while preparing for a comeback in Florida.
He underwent surgery and is expected to make a full recovery but will miss the upcoming Masters tournament.
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