Back in 2019, Tiger Woods stood proudly in the White House, wearing the Presidential Medal of Freedom—a personal honor bestowed by Donald Trump himself. Their friendship had already spanned decades, built on a mutual love of golf and respect for each other’s accomplishments. But in 2025, their connection has taken a dramatic new turn—one that no one saw coming.
Woods is now dating Vanessa Trump, the ex-wife of Donald Trump Jr. The couple has been together since Thanksgiving 2024, and their relationship has turned heads across the sports and political worlds. Many speculated about how Trump Sr. would react to this bombshell pairing. Now, the former president has finally broken his silence—and his reaction is nothing short of surprising.
When asked about Woods’ relationship with Vanessa, Trump delivered a brief yet telling five-word message: “Let them both be happy.” His response comes just days after Woods made the relationship Instagram official, requesting privacy from the media. However, Trump’s public blessing takes this high-profile romance to an entirely new level.
But Trump didn’t stop there. He elaborated with warmth, saying, “I love Tiger and I love Vanessa.” This unexpected display of support set the tone for his response, putting to rest any speculation about lingering tensions.
An Unlikely Romance in the Spotlight
Vanessa Trump, who shares five children with Donald Trump Jr., divorced in 2018 after 13 years of marriage. While their split was amicable, her new relationship with Woods has brought fresh attention to the Trump family’s personal lives. However, according to insiders, Trump Sr. has no objections. “Trump knows about him dating Vanessa and is said to approve,” a source told Page Six months ago. Now, his public endorsement leaves no doubt.
Perhaps the most revealing detail is how Woods personally informed Trump about the relationship before it became public. “Tiger called me a few months ago and told me,” Trump admitted. This gesture speaks volumes about the deep respect between them—Woods clearly valued Trump’s reaction enough to deliver the news directly.
A Friendship Forged on the Golf Course
Woods and Trump have shared a strong bond over the years, one that began on the golf course. Their rounds together at various Trump-owned courses solidified their friendship. One of the most memorable moments came in 2019 when Woods, Trump, and golf legend Jack Nicklaus played together in Jupiter, Florida. Trump has long been an admirer of Woods’ game, even naming a villa after him at his Doral property in Miami.
Their mutual admiration extended beyond the greens. In 2019, Trump publicly predicted Woods’ return to major championship glory—an accurate forecast as Woods went on to win the Masters that same year. Woods, in turn, has praised Trump’s golfing ability, once noting, “For a person who’s 70 years old, he hits it hard. He can rip it and hit it.”
A New Chapter for Woods and Vanessa
Beyond their high-profile pasts, Woods and Vanessa Trump reportedly share a deep connection. A source close to the couple told Page Six, “They have a lot in common. They both know how to navigate public scrutiny, they prefer to keep their private lives private, and they share similar values.” Both are parents as well—Woods’ son Charlie and Vanessa’s daughter Kai are promising junior golfers, a common passion that has helped bring them closer together.
As the world watches this unexpected romance unfold, Trump’s words remain clear: He has given his blessing, and he wants the world to move on. But with Woods and Vanessa now stepping into the spotlight together, that might be easier said than done.
