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Inside Tiger Woods' 50th Birthday Bash: Golf Legend Celebrated Major Milestone with Glamorous Girlfriend Vanessa Trump and A-List Pals

tiger woods, kai trump, vanessa trump
Source: mega, kaitrumpgolfer/instagram

Tiger Woods partied with girlfriend Vanessa Trump and her daughter Kai.

Jan. 15 2026, Published 2:52 p.m. ET

Tiger Woods partied with some of his closest pals, including steady girlfriend Vanessa Trump, RadarOnline.com can share, as the golf legend celebrated his 50th birthday, as well as the 30th anniversary of his charitable foundation.

Woods, who turned the big 5-0 on December 30, could soon be planning another fancy shindig... their wedding.

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Woods Celebrates His Milestones

tiger woods
Source: MEGA

Woods was celebrating his birthday and the anniversary of his self-named foundation.

Woods mingled with some high-profile friends and family at a celebration in Palm Beach, Florida, for his Tiger Woods Foundation.

Over 300 people dined on the finest sushi and steaks and enjoyed a private acoustic performance from Jon Bon Jovi.

Mixed in among the attendees were Woods' girlfriend, Vanessa Trump, and her golf-loving daughter, Kai. The 18-year-old shared snaps of her and her mom together before the party in their dazzling dresses.

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Source: kaitrumpgolfer/instagram

Vanessa, 48, opted for a low-cut black dress and red heels, in keeping with the color theme of the party, while Kai took the color scheme one step further in a floor-length, all-red dress.

Kai's left wrist was heavily wrapped as she recovers from surgery to fix injuries to the stabilizing tissues of her ECU tendon and damage to her triangular fibrocartilage complex.

Meanwhile, host Woods kept it classy in a dark tux blinged out with a red tie and red pocket square.

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Are Wedding Bells in the Future?

Photo of Vanessa Trump and Tiger Woods
Source: @tigerwoods/instagram

Vanessa and Tiger's relationship is rumored to be headed to the next level.

Woods and Vanessa, the ex of Donald Trump Jr., have kept their romance largely out of the spotlight. But Radar has learned the two are "deeply in love" and already planning a dream wedding – this time at a slightly larger venue, the White House.

"They're not playing around," said a source. "They've both been through scandal, heartbreak and headlines – and somehow found peace in each other."

Though no official engagement has been announced, whispers of a presidential venue have already begun.

"The symbolism is powerful," noted another insider. "A Trump returning to the White House… but this time, for love."

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Love Story

vanessa trump
Source: mega

Vanessa met the golfer at their kids shared school.

Woods and Vanessa's romance began after they met each other while attending events for the Benjamin School, the pricey Florida private school their children attended.

Not long after, she was seen walking alongside Woods as he supported son Charlie at school golf tournaments and later at Palm Beach social functions together.

In just a little over a year of dating, one insider claimed Woods and Vanessa's relationship has become "really, really serious" – and allegedly has the iconic athlete considering getting married for a second time.

"It's a much more mature relationship than anything he's been in before, and he's going into it with his eye on something long-term," the insider claimed. "Ideally, for the rest of his life."

The source added: "Of everyone he's dated since (his ex-wife) Elin, I'd say Vanessa is the closest thing to a soulmate he's ever had."

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Standing By Her Man

tiger woods, vanessa trump
Source: @tigerwoods/instagram

Vanessa has stood by his side during his rehab.

Woods has had some extra free time to focus on the relationship, as he continues to rehab from yet another back surgery last year. Luckily for him, Vanessa has stayed by his side.

According to the insider, Don Jr.'s ex-wife "came into (Woods') life at just the right time."

"She showed up as he was seriously considering what happens next in his career," the source close to Woods told the Daily Mail. "She has added so much stability on the home front, and he gushes about her influence in his life."

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