Tiger Woods is Dating Trump. And It's Serious.
President Trump Presents the Medal of Freedom to Tiger Woods, 2019. Photo courtesy of The White House. Public domain.
Tiger Woods is back in the headlines, but not for what you'd expect. There are no scandals or golf comebacks on Woods's horizon; instead, it's his newest (and possibly most eyebrow-raising) romance that has fans, gossip columnists, and political watchers doing a double take. Woods, 49, just went Instagram official with none other than Vanessa Trump, ex-wife of Donald Trump Jr. and former first daughter-in-law of President Donald Trump. The photo dump was cozy, romantic, and unmistakably serious.
Is this relationship all soft-focus snapshots and smiling selfies? Or is this something more layered than just a celebrity couple's soft launch?
From Mar-a-Lago to Match Play
Vanessa Trump, born Vanessa Kay Pergolizzi, is no stranger to headlines. After an introduction at a fashion show by Trump Sr., the former model and actress married Donald Trump Jr. in 2005 — at Mar-a-Lago, naturally — and spent 12 years inside America's most infamous political dynasty. She and Trump Jr. share five children and officially split in 2018.
Since their divorce, Vanessa Trump has kept a relatively low profile. She's been spotted occasionally with the Trump family and attended the President's second inauguration in January. But mostly, she's been raising her kids in Jupiter, Florida — the same area where Tiger Woods resides with his two children from his previous marriage to Elin Nordegren.
That's not the only overlap. Vanessa Trump's daughter, Kai Trump, and Woods' son, Charlie, both attend school in Palm Beach and play competitive golf — which may have been the original spark for this unexpected pairing. The two families were seen together at a recent golf event in San Diego and again at Woods' TGL indoor golf league event in Florida.
An Albatross in Amore?
Some insiders claim Woods and Vanessa began dating just before Thanksgiving 2024, quietly building a bond around their shared status as parents under the spotlight. Others say it's been longer — and much more serious than anyone guessed.
An anonymous source close to the couple told Page Six that the couple started as friends but shared undeniable chemistry that evolved naturally. "They're a good match; they're level-headed, they like to avoid drama, they share a lot of the same values."
Sources close to the couple suggest they've even begun integrating their families. And in a surprising show of familial unity, even Trump Jr. seems to approve. The Page Six insider shared that Trump Jr. "fully supports" the new couple, adding that Trump Jr." has obviously dated other people since their split so as long as Tiger treats Vanessa and their kids with respect, he's good with it."
It helps that the President has been a big fan of Wood's for years, having long referred to him as "a true legend," as reported by the LA Times. The President and the golf champion have played together multiple times, and in 2019, Trump awarded Woods the Presidential Medal of Freedom.
The Tiger Woods of It All
Even amid this blossoming romance, Tiger Woods is a man whose name carries a shadow of personal scandal.
His split from Nordegren in 2010 followed one of the most infamous cheating scandals in sports history: over a dozen women came forward alleging affairs with the golf superstar, prompting Woods to enter rehab for sex addiction and sparking a media firestorm that nearly derailed his career, according to US Magazine.
Since then, Woods has carefully navigated his return to public life — with mixed success. His post-scandal romantic life included a high-profile relationship with restaurant manager Erica Herman; that relationship ended in a messy legal battle involving a nondisclosure agreement and allegations of sexual harassment, as reported by US Magazine. Herman ultimately dropped the suit and stated she was not a victim of abuse, but the headlines were once again unavoidable.
Now, with Vanessa by his side, Woods appears to be trying something different: a relationship grounded in shared experience — two single parents, both seasoned by scandal, navigating elite circles in the same South Florida bubble.
The Tiger-Trump pairing has turned a few cocktail circuits and fairways into headline-grabbing battlegrounds. And in true Trump-adjacent fashion, they're not shying away from it.
References: Trump called Tiger Woods a 'true legend.' Now golfer is dating Vanessa Trump, president's ex-daughter-in-law | Who is Vanessa Trump? What to know after relationship with Tiger Woods goes public | Tiger Woods confirms Vanessa Trump relationship on social media: 'Love is in the air' | Tiger Woods confirms romance with Vanessa Trump: 'Life is better with you' | Tiger Woods' ex-caddie shares brutal treatment before relationship ended in disgrace | Tiger Woods' Dating History: The Golfer's Marriage, Mistresses, Girlfriends and More
