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Secret signs Tiger Woods was dating Vanessa Trump from Kai pic to hanging out at Mar-a-Lago weeks before fling exposed


DONALD Trump Jr.’s ex has been secretly dating Tiger Woods for months – and there have been hidden clues about the lovebirds’ fling.

Woods and Vanessa Trump have reportedly been seeing each other since before Thanksgiving, but have yet to make their relationship public.

Tiger Woods and Kai Trump walking near cars.

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Kai Trump, Tiger Woods, and Vanessa Trump arriving at the Genesis Invitational 2025 at Torrey Pines Golf Course in La Jolla, California, on February 16, 2025Credit: Getty
President Trump presenting Tiger Woods with the Presidential Medal of Freedom.

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Woods receiving the Presidential Medal of Freedom during a ceremony at the White House in Washington DC on May 6, 2019Credit: AFP
Kai Trump and Tiger Woods walking at a golf course.

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Vanessa, Kai, and Tiger Woods at the Genesis InvitationalCredit: Getty

However, a look back at the pair’s last four months reveals signs the golf legend and the President’s former daughter-in-law were an item – and it’s mostly thanks to Vanessa’s daughter, Kai Trump.

Kai, 17, is a competitive golfer and social media star who has committed to playing at the University of Miami in the fall.

The teen reportedly goes to the same Florida school as Woods’ teenaged kids Charlie, who is also a golfer, and Sam.

Last month, Kai and Vanessa, 47, attended the Genesis Invitational, which is hosted by Woods, in San Diego, California.

Woods, 49, was pictured walking and talking with Kai’s entourage, including her mom, during the tournament.

The athlete, widely considered one of the best golfers of all time, has been an avid supporter of Trump as the President begins his second presidency.

However, he still raised eyebrows when he was spotted spending time with the President’s granddaughter and giving her some pointers on the range.

Woods has been getting cozy with the Trump family for years, starting when he attended events at golf courses owned by Trump in the early 2000s.

During Trump’s first presidency, Woods was often seen golfing with him at Trump International Golf Club in Florida.

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Woods was recently pictured on the golf course at Mar-a-Lago with the President on February 9.

On February 20, Woods was honored at a Black History Month reception at the White House.

It’s unclear how Vanessa and Woods met.

The couple reportedly lives only about 20 minutes away from each other, according to the Daily Mail.

“She comes to his place on Jupiter Island. They’re not living together,” the outlet reported.

Vanessa Trump’s dating history

Vanessa Trump, the ex-wife of Donald Trump Jr., is reportedly dating golf legend Tiger Woods.

Here’s a look at Vanessa’s past relationships:

  • Valentin Rivera (1990s) – a member of the Latin Kings gang
  • Leonardo DiCaprio (1998) – Hollywood actor
  • Khalid bin Bandar bin Sultan Al Saud (1998-2001) – Saudi prince
  • Donald Trump Jr. (2003–2018) – President Donald Trump’s son
  • Tiger Woods (2024-present) – golf legend

“She comes over and spends the night and leaves in the morning. Maybe a few nights a week.”

When asked about his ex-wife’s new relationship, Donald Trump Jr. reportedly said he was “cool” with it, according to People.

Vanessa Trump, Kai Trump, and Donald Trump Jr. at the Republican National Convention.

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Vanessa, Kai, and Donald Jr. at the Republican National Convention in Milwaukee, Wisconsin, on July 17, 2024Credit: Getty
Donald Trump Jr. and Vanessa Trump at an event.

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Donald Trump Jr. and Vanessa Trump at Trump World Towers in New York City in April 2006Credit: Getty
Vanessa Trump, Donald Trump Jr., and their daughter Kai being interviewed.

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Vanessa, Donald Trump Jr., and Kai at the White House Easter Egg Roll in April 2017Credit: Getty

Donald Jr. has also been busy with a new relationship with socialite Bettina Anderson. The two were seen schmoozing up together at the President’s joint address to Congress last week.

Vanessa and Donald Jr. were married for 12 years and have five kids together.

However, the New York City native boasted a wide-ranging dating history before she tied the knot with Donald Jr. in 2005.

VANESSA TRUMP’S LOVE LIFE

During her high school years, the model dated a gang member named Valentin Rivera and went to prom with him before he was sent to prison for various crimes, according to Page Six.

When she was 20, Vanessa was linked to A-list actor Leonardo DiCaprio.

She then dated Saudi prince Khalid bin Bandar bin Sultan Al Saud for three years before the couple broke up in 2001.

Vanessa has kept her love life out of the spotlight after she filed for divorce from Donald Jr. in 2018.

If Woods and Vanessa show their relationship on social media or out together, it’ll be her first public boyfriend since her marriage.

Charlie and Kai are both set to compete at the Junior Invitational golf tournament in Sage Valley, South Carolina, next week – meaning Vanessa and Woods might be seen together for the first time since their relationship was revealed.

President Donald Trump and Tiger Woods at a Black History Month reception.

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Trump and Woods at a Black History Month reception at the White House on February 20, 2025Credit: Getty
Donald Trump Jr. and his wife Vanessa at a party.

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Donald Jr. and Vanessa at a party celebrating The Apprentice Season 5 finale in Los Angeles on June 5, 2006Credit: Reuters
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