Tiger Woods is Rumored to Be Dating Donald Trump Jr.'s Ex-Wife, Vanessa Trump
Complex - Tiger Woods is reportedly dating Vanessa Trump.
A source told TMZ that the golfing pro and Trump began seeing each other around Thanksgiving 2025. However, they’ve kept their romance private by spending time at Woods’ Jupiter, Florida home.
Vanessa is a Trump by marriage. The 47-year-old was married to Donald Trump Jr. from 2005 to 2018, and during that time, the exes welcomed two children together, Kai Madison and Donald Trump III.
Woods has been in the Trumps’ orbit for years, having recently played golf with President Donald Trump after his mother, Kultida Woods, passed away in February. Woods’ son, Charlie, and Trump’s daughter, Kai, also both play golf at The Benjamin School in Florida.
I'm not sure why, but when I saw this rumor, the first thing that popped in my head was, "Damn... Vanessa Trump is not living a real life". Think about it. If these Tiger Woods rumors are true. Especially if Tiger Woods and Vanessa Trump (who apparently never ditched her ex-husband's name) end up being together for a significant amount of time. Or maybe even get married. Vanessa Trump is just living an all-time fake life. It's a really damn cool one. She's very much living life to the fullest. And I'm sure she's experienced an endless amount of cool shit. But going from being married to Donald Trump Jr. for 13 years to dating Tiger Woods... given there was some time between the two... Tiger and Don Jr. just aren't real people. They're both so so so far above even celebrity status. Even before Trump was President, him and Tiger were both so far beyond rich that they couldn't even begin to live life like halfway regular people. They don't go to the grocery store. They wouldn't have to tie their shoes for the rest of their lives if they didn't want to. They probably don't. And they probably both get to live their lives running on an awesome cocktail of experiment drugs we've probably never even heard of. I'm sure Don Jr. gets to take some sort of Limitless drug every morning. Tiger Woods has been on super fentanyl ever since he got done cosplaying as a Marine. He was a full-blown zombie long before he drove that car off a cliff.
My point is, nothing about anything that Donald Trump Jr. or Tiger Woods has done in the past however many years has resembled normalcy in the slightest. I can't even imagine what it must be like to date, or be married to either of them. So I guess that makes sense for Tiger. To date a woman who's used to living a completely surreal lifestyle. It makes sense for Vanessa too. You can't just go back to normal life after divorcing the President's son. When you think about it, they're really the perfect match.
From Don Jr.'s perspective, and maybe I'm wildly wrong here, but I can't help but think he loves this. I'm sure respects celebrity. He respects greatness. He respects golf. Now that he's running in a group of people who literally run the United States, I doubt there's anybody he views as a "threat", or as "above him". I bet he's proud as hell to have been married 13 years to a woman that Tiger Woods deems acceptable to date.
Or maybe I'm way off. Maybe Don Jr. hates this. As much as he respects greatness, and respects golf. If he's like his dad at all, he doesn't like to be second best at things. And I bet if there's one regular person thing he'd love to have, but can't simply buy with money, it's a world-class golf game. I know he's probably a fine golfer in his own right. But he's not Tiger Woods. Maybe the fact that his ex-wife is dating somebody who could run circles around him on the course... maybe that would be kinda tough to swallow? If there's one type of person I could see him feeling inadequate around, it's a professional golfer. Not just any golfer. Tiger Woods. A golfer with a certified hammer dick.
But I still doubt it. I bet Don Jr. is eating this shit up. I'm pretty sure Tiger and the Trump's are friends. Or at least friendly. Honestly they seem like the type of people to go on vacation together, wives and ex-wives included like one big absurdly wealthy family.
And again… according to People, Don Jr. is reportedly "cool" with the whole thing.
Men's Journal - Donald Trump Jr. isn’t upset about his ex-wife Vanessa Trump’s new relationship with golfing legend Tiger Woods.
That’s according to People, which reported that Trump Jr. had a 1-word response to the news. That word is “cool.”
People reported, through a source, that Trump Jr. is “cool” with Vanessa Trump’s new relationship, which People confirmed with a source close to the president’s family.
But Tiger Woods and Vanessa Trump… what a power couple. Now that Tiger Woods has suffered yet another devastating achilles injury, you gotta think his professional golf career is all but over. Feels like we're just a domino or two falling away from Tiger Woods being appointed to a position in the White House. Crazier things have happened in government. I'm halfway expecting my boss to call a meeting any day now to let us know he's accepted a position in Trump's cabinet. Maybe Tiger Woods high as balls off pain pills has something to offer our country as well.