Tiger Woods and Vanessa Trump’s Friends Are ‘Whispering’ About a ‘Whirlwind Engagement’

Tiger Woods is madly in love with new girlfriend Vanessa Trump. The legendary golfer is looking to spoil her like a princess this summer, and a source exclusively tells In Touch that pals are whispering that a whirlwind engagement could well be in the cards.

“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 says. “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 continues, “Tiger’s got a reputation for being cheap, even though he’s worth nearly a billion and a half, but with Vanessa he’s not cheap at all. It’s a free for all with the spending suddenly, he clearly wants to impress her. And he’s certainly enjoying himself.”

The insider adds that Tiger, 49, is “grinning from ear to ear these days,” and even though he and Vanessa, 47, haven’t been dating for “all that long,” the PGA tour champion is “saying 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 explains.

Tiger and Vanessa, who was previously married to Donald Trump, Jr., have been quietly building a relationship that’s finally come into the light, and the spark is mutual. Sources say the couple began seeing each other around Thanksgiving 2024, after connecting through their teenagers at school and shared appearances at golf events.

The couple officially confirmed their romance in March 2025 when Tiger posted two 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 that sentiment via her Instagram Story.

Photo by Alec Tabak – Pool/Getty Images.Vanessa Trump
Shortly after, Vanessa’s former sister-in-law, Ivanka Trump, commented, “So happy for you both!”

The pair share strong ties to the golf community. Each has teens (Tiger’s Sam and Charlie; Vanessa’s daughter Kai) who attend the same school and play in rival junior golf tournaments. Their shared interest in their children’s athletic pursuits has clearly strengthened their bond.

“I love Tiger and I love Vanessa,” President Donald Trump said, per 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 president, 78, 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 for the pair’s relationship is especially poignant. Tiger continues to recover from a ruptured Achilles tendon, which cut short his 2025 season after a March announcement. On her end, Vanessa, who shares five children with Trump Jr., finalized her divorce in 2018.