Back in 2019, Tiger Woods stood proudly at the White House. He wore his Presidential Medal of Freedom with dignity. This prestigious award came directly from Donald Trump himself. Their friendship had already spanned decades at that point. Yet no one could have predicted the interesting twist their relationship would take years later.

Fast forward to 2025, and Woods has found love with Vanessa Trump. They have been together since 2024 Thanksgiving. She happens to be the ex-wife of Donald Trump Jr. This unexpected pairing initially raised eyebrows across the golf world. Many wondered how President Trump would react to this surprising development. His response has now put those questions to rest. Initially. An insider had confirmed to Page Six, “[President] Trump knows about him dating Vanessa and is said to approve.” But now, Donald Trump himself shared his thoughts.

When recently asked about the relationship, President Trump offered a simple 5-word message, “Let them both be happy.” His supportive words came just days after Woods made their romance Instagram official. He had requested privacy in his announcement. Yet Trump’s public endorsement takes this high-profile relationship into a new dimension.

President Trump didn’t stop at a simple blessing for the couple. He shared more detailed thoughts about the situation. “I love Tiger and I love Vanessa,” he stated with genuine warmth. This affectionate opening set the tone for his entire response.

He then addressed the previous marriage directly. “Vanessa and Don had a good relationship,” Trump explained. “They broke up quite a while ago.” His calm acknowledgment showed no lingering tension about the divorce. Vanessa and Trump Jr split in 2018 after 13 years of marriage. They have five children together.

Perhaps most revealing was Trump’s next disclosure. “Tiger called me a few months ago and told me,” he shared. This personal phone call speaks volumes about their relationship. Woods felt it necessary to inform Trump before the news went public. Such consideration demonstrates deep respect between the two men.

The source close to the couple confirmed to Page Six that “They have a lot in common. They’ve both gotten used to public scrutiny. They both know how to keep their private life private. They’re both parents. They’re a good match; they’re level-headed, they like to avoid drama, they share a lot of the same values.”

For those who might not know, the bond between Woods and President Trump stretches back many years. Their connection primarily developed on the golf course.

A friendship built through golf and mutual admiration

They’ve played numerous rounds together at various Trump properties. Both men share a genuine passion for the game. One particularly memorable outing took place in 2019. Woods joined Trump and golf legend Jack Nicklaus for a round in Jupiter, Florida. This gathering brought together three towering figures from different worlds. 

Trump has consistently shown admiration for Woods’ abilities. He even named a villa after Woods at his Doral property in Miami. The president once publicly predicted Woods’s comeback to winning majors. This prediction proved accurate when Woods claimed the 2019 Masters title. Woods has equally praised Trump’s golfing prowess. “For a person who’s 70 years old, he hits it hard,” Woods once remarked. “He can rip it and hit it.” Their mutual respect extends beyond the golf course. Trump awarded Woods the Presidential Medal of Freedom in 2019.

Both families share a passion for golf. Woods’s son Charlie and Vanessa’s daughter Kai are promising junior golfers. These common interests provided natural grounds for their relationship to develop.