When Kai Trump showed up at the Sofi Center during TGL, cheering for Tiger Woods’s team in a cozy dark green SDR sweatshirt, it seemed like just another moment of fan support. Standing on the sidelines alongside her mother, Vanessa Trump, Kai looked genuinely excited to be there. But looking back, was this just about golf, or is there more to the story?

This wasn’t the first time Kai was spotted at a Woods-related event. In recent weeks, both Vanessa and Kai have been showing up at tournaments where Woods was in action, including The Genesis Invitational and TGL matches. Sure, Kai is a young golfer herself, but their repeated presence at Woods’s events is definitely raising eyebrows.

And now, thanks to some fresh dating rumors, it looks like there might be more to the story.

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Wait… Tiger Woods and Vanessa Trump?

Yes, you read that right. According to Daily Mail and People Magazine, Tiger Woods is “secretly dating” Vanessa Trump—yes, Donald Trump Jr.’s ex-wife. And apparently, this has been going on since Thanksgiving 2024.

A source close to the family spilled some details, saying: “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.”

And in case you were wondering—yes, Don Jr. is reportedly “cool” with it.

Now, here’s where it all starts to click. Kai Trump and Woods’s children, Charlie and Sam, attended the same school. That means they were already in each other’s circle, which could explain why Kai and Charlie have been spotted together so often at golf events. But with this new dating rumor surfacing, their joint appearances start to make even more sense. It’s not just about golf anymore—it’s about family connections. 

Who is Vanessa Trump?

For those who don’t know, Vanessa Trump isn’t just Donald Trump Jr.’s ex-wife. She used to model for Wilhelmina Models, made a brief appearance in Something’s Gotta Give (2003), co-founded the nightclub Sessa, and even launched her own handbag line, La Poshett.

When it comes to past relationships, she’s been linked to some big names—including Leonardo DiCaprio in 1998 and Saudi prince Khalid bin Bandar bin Sultan Al Saud from 1998 to 2001. She married Don Jr. on November 12, 2005, at Mar-a-Lago, and the two were together for 13 years before they split in 2018. Since then, Don Jr. has moved on with former Fox News host Kimberly Guilfoyle, while Vanessa has largely stayed out of the dating spotlight.

On the other hand, Woods’s romantic history has been just as eventful. Firstly, it was his very public split from Elin Nordegren in 2010 (following those infamous cheating scandals), and then it was his dating life with Erica Herman that made the waves. 

As of now, neither Woods nor Vanessa Trump has confirmed anything, but their rumored romance has definitely caught the internet’s attention. Whether they go public or keep things private, one thing is for sure—this adds a whole new layer to Kai Trump and Charlie Woods’s frequent appearances together.