Photo-Illustration: Intelligencer; Photos: Getty Images
Elections have consequences, and one of the many unfortunate things about the outcome of the 2024 race is that we all have to know things about the Trump family, like Barron Trump’s height and the fact that Lara Trump exists. I regret to inform you that there is now another lesser-known presidential daughter-in-law making news. Vanessa Trump is dating Tiger Woods, the legendary golfer and occasional generator of tabloid gossip. Here’s everything you need to know to know about these lovebirds to maintain your Trump family-drama fluency.
Who is Vanessa Trump?
Vanessa Trump is Donald Trump Jr.’s ex-wife, and thus President Trump’s former daughter-in-law.
How long have Vanessa Trump and Tiger Woods been dating?
It seems their relationship began last fall. On March 13, 2025, the Daily Mail reported that Woods had “sensationally started dating” Trump, and the pair were “quickly becoming golf’s new power couple”:
A source said: ‘Tiger and Vanessa have been seeing each other since just before Thanksgiving.
‘She comes to his place on Jupiter Island. They’re not living together. She comes over maybe a few nights a week.’
‘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.’”
Have Vanessa Trump and Tiger Woods confirmed their relationship?
Yes. On March 23, 2025, Woods put up a somewhat confusing Instagram post that simultaneously declared, “Yes, I am dating Vanessa Trump” and “My love life is none of your business.”
How did Vanessa Trump and Tiger Woods meet?
We don’t know the details, but they run in the same circle. They both live in the Palm Beach, Florida, area, their kids play golf, and their teens attend the same $38,595 a year private school, the Benjamin School.
How old are Vanessa Trump and Tiger Woods?
Trump is 47 and Woods is 49, making this a surprisingly age-appropriate celebrity pairing.
What’s Vanessa Trump’s backstory?
Vanessa Haydon was born to a wealthy family. Her father, Charles Haydon, was an attorney who worked with high-profile clients like Marilyn Monroe. Her mother, Bonnie Haydon, ran Kay Models Agency. Vanessa grew up in a townhouse on Manhattan’s Upper East Side and started modeling as a child.
Vanessa attended the Dwight School and was “not a particularly distinguished student,” according to the New York Times. The paper also noted, “In her high school yearbook, Ms. Trump was described both as most likely to ‘be on Ricki Lake’ and to ‘get a divorce.’”
How did Don Jr. and Vanessa meet?
They were introduced by Donald Trump Sr. — twice — at a 2003 fashion show for the Kmart brand Thalia at Capitale. Vanessa shared the story with the Times in 2006 (brace yourself for language that, while incredible in context, is no longer acceptable in 2025):
“I’m at this fashion show,” Vanessa Trump said, recalling their meeting in 2003. “Donald Trump comes up to me with his son: ‘Hi, I’m Donald Trump. I wanted to introduce you to my son Donald Trump Jr.’”
The three engaged in a brief, awkward conversation.
At intermission, the elder Trump again noticed a gorgeous girl nearby.
“Donald comes back up to me again, ‘I don’t think you’ve met my son Donald Trump Jr.,’” Vanessa Trump recalled. She remembers responding, “Yeah, we just met, five minutes ago.”
Six weeks later, at a birthday party at a New York restaurant, they were introduced a third time, this time by a mutual friend. Neither remembered the other. “We talked for an hour,” she recalled.
Then suddenly, something clicked: Wait, you were at that fashion show. Wait, you’re “the one with the retarded dad!” Vanessa blurted out.
How long were Don Jr. and Vanessa Trump married?
They were married for 13 years. In 2004, Don Jr. popped the question at a New Jersey mall with a ring he got for free, just like every little girl dreams of. Per the Times:
The younger Mr. Trump proposed with a $100,000 ring that he got for free by agreeing to stage his proposal before paparazzi at the Short Hills Mall where the jeweler of the ring, Bailey Banks & Biddle, was located. The move frustrated his father, who complained about it on Larry King Live. (The publicity ploy ultimately didn’t work. By 2009, Bailey Banks & Biddle was in bankruptcy and the Short Hills location was closed.)
Vanessa and Don Jr. got married on November 12, 2005, at Mar-a-Lago. They divorced in 2018, and Vanessa has remained close to the Trump family.
Do Vanessa and Don Jr. have kids?
Yes, they have five children: Kai, 17; Donald III, 16; Tristan, 13; Spencer, 12; and Chloe, 10.
Do I need to know anything about them?
For now, not really. Kai Trump, the president’s eldest grandchild, is a competitive golfer who already has an endorsement deal and has committed to playing golf at the University of Miami when she starts college in 2026. During the 2024 campaign, she delivered a speech supporting her grandfather at the Republican National Convention and become a MAGA influencer, with 3 million TikTok followers. She seems poised to be one of the more prominent Trump family members, but at the moment she’s a 17-year-old high-school student.
Why did Vanessa Trump and Don Jr. break up?
Perhaps that’s none of our business, but President Trump offered up his theory while discussing Vanessa’s new relationship with White House reporters on April 1, 2025.
“I happen to think the relationship was hurt very badly by the witch hunt that went on — Russia, Russia, Russia — all the crap that they put Don through, who knew nothing about it,” the president said.
Does Don Jr. have a girlfriend?
Yes, but it may not be the woman you’re thinking of. Don Jr. and Kimberly Guilfoyle got engaged in 2020, and their relationship ended sometime last year. President Trump made his son’s ex-fiancée the U.S. ambassador to Greece, and now Don Jr. is dating Bettina Anderson.
Has Vanessa Trump dated any other notable people?
Yes, her alleged romantic history definitely has a Mad Libs quality to it. She dated Latin Kings gang member Valentin Rivera in high school; he told the New York Post that Vanessa visited him while he was serving time for assault at Rikers Island, and he provided a photo of Vanessa dancing with him at her senior prom.
In 1998, “Page Six” reported that Vanessa was spotted on a date with Leonardo DiCaprio, but months later, a New York Magazine story suggested she started the false rumor herself.
Vanessa also dated Saudi prince Khalid bin Bandar bin Sultan Al Saud until 9/11 doomed their love affair … if you believe this 2018 “Page Six” report:
“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,” a source told Page Six.
… His father, Bandar bin Sultan Al Saud, was Saudi Arabia’s ambassador to the US from 1983 to 2005, with ties so close to the Bush family he was known as “Bandar Bush.”
He was suspected of indirect ties to al Qaeda and associates of the 9/11 hijackers, but there was no evidence that he knowingly provided support for the attacks. He insisted, “Saudi Arabia has nothing to hide” and 9/11 was “the worst thing to happen to us.”
Any there any other weird things I should know about Vanessa?
I’m beginning to think I’m incapable of summing up the rich and fascinating life of Vanessa Trump in this little explainer. But I’d like to bring your attention to two other Vanessa curios.
First: a People story headlined “Vanessa Trump Reportedly Inherited Millions From Family’s Marinara Sauce Deal Before Don Jr. Split.”
Second: the opening credits to the Nancy Meyers film Something’s Gotta Give, in which models gallivant around New York to Crazy Town’s “Butterfly.” Vanessa shows up only briefly at the 0:57 mark in the video below, but you should watch the whole thing to experience 2003 in its purest form.
Speaking of the early 2000s, what happened with that Tiger Woods scandal?
Rachel Uchitel. Jaimee Grubbs. Kalika Moquin. Mindy Lawton. If these names ring a bell, you were probably reading way too many gossip blogs in 2009. Basically, Tiger Woods’s golden-boy image was shattered after the National Enquirer reported that Woods was having an extramarital affair, and two days later, the golfer crashed his car into a tree near his home. The story spiraled from there, and eventually more than a dozen alleged mistresses came forward.
Woods publicly apologized several times, but his wife Elin Nordegren divorced him in 2010.
MARK RALSTON/AFP via Getty Images
Do Tiger and Elin have kids?
Yes. Tiger has two children from his marriage to Elin: a 17-year-old daughter, Sam Alexis, and a 16-year-old son, Charlie.
How does President Trump feel about Tiger Woods dating Vanessa?
He said Woods called him and told him he was dating his ex-daughter-in-law “a few months ago,” and he’s happy for them.
“I love Tiger and I love Vanessa,” Trump said. “He told me about it, and I said, ‘Tiger, that’s good, that’s good.’ I’m very happy for both. Just let them both be happy. Let them both be happy. They’re both great.”
Donald Trump gave Tiger Woods his stamp of approval after the golf champion announced his new relationship with Vanessa Trump, ex-wife of Donald Trump Jr. pic.twitter.com/4rhNamncny
— E! News (@enews) April 1, 2025
What did Don Jr. say about the relationship?
He has yet to comment publicly, but he’s “cool” with his ex dating Tiger Woods, according to People.
What did other Trumps say about the relationship?
Ivanka Trump left this comment on Woods’s Instagram announcement:
How are Barack and Michelle Obama involved in all this?
The Obamas’ company, Higher Ground, was in talks to produce a biopic about the golfer based on the Kevin Cook book The Tiger Slam: The Inside Story of the Greatest Golf Ever Played, as Deadline reported in March. The Obamas haven’t publicly commented on the project or on Woods’s personal life.
So could Tiger Woods wind up related to Donald Trump or something?
Sort of? If Tiger and Vanessa marry, Woods will be the First Grandkids’ stepfather. Trump spent two decades openly shipping Tom Brady and Ivanka, only for his eldest daughter to marry Jared Kushner. So of course Trump is happy that Tiger is dating Vanessa: This may be as close as he gets to having a sports GOAT for a son-in-law.
