Tiger Woods 'Planning' to Marry Girlfriend Vanessa Trump, Insider Reveals: He's 'Fully Enmeshed' in Her World

Tiger Woods is head over heels for his new girlfriend, Vanessa Trump. The legendary golfer plans to treat her like royalty this summer, and friends are hinting at a possible engagement, according to a report.

"Tiger is fully enmeshed in Vanessa's world. He was just at the White House with her and was welcomed with open arms by everyone," the insider revealed.

The insider added: "She has a very high-flying circle of friends, and he's in with them too and planning to rent a massive super yacht this summer to cruise around the Mediterranean with Vanessa and a bunch of her friends."

The source added that while Woods, 49, is known for being thrifty despite his nearly $1.5 billion net worth, he's has been taking caution to the wind with Trump. "It's a free for all with the spending suddenly; he clearly wants to impress her. And he's certainly enjoying himself," the insider dished.

According to the insider, Woods is "grinning from ear to ear" these days. Although he and Trump, 47, haven't been dating long, the PGA tour champion insisted this is "the best relationship he's ever had."

"He's over the moon about her and saying he plans to marry her so people in his world are expecting it to happen fairly soon," the source explained.

Woods and Trump, who was previously married to Donald Trump Jr., quietly navigated their relationship, but now it's blossoming into the spotlight. Sources said the couple started seeing each other around Thanksgiving 2024 after their teenagers connected at school and during golf events.

They confirmed their romance in March when Tiger shared two affectionate photos on social media with the caption: "Love is in the air and life is better with you by my side! We look forward to our journey through life together." Vanessa echoed his sentiment via her Instagram Story.

Shortly after, Vanessa's former sister-in-law Ivanka Trump expressed her joy by commenting, "So happy for you both!"

The couple share strong ties to the golf community, as their teenagers — Tiger's Sam and Charlie, and Vanessa's daughter Kai — attend the same school and compete in rival junior golf tournaments. Their mutual interest in their children's athletic pursuits appears to have strengthened their bond.

"I love Tiger and I love Vanessa," President Donald Trump said, according to People. "He and I have a very special, very good relationship with Tiger. I played golf with him a couple of times over the last month, and he's a fantastic guy and a fantastic athlete."

The 78-year-old president continued, "He told me about it, and I said, 'Tiger, that's good, that's good.' I'm very happy for both. Just let them both be happy. Let them both be happy. They're both great."

The timing of their relationship is particularly meaningful. Tiger is on the mend following a ruptured Achilles tendon, which cut short his 2025 season after a March announcement. Meanwhile, Vanessa, who shares five children with Trump Jr., finalized her divorce in 2018.