Insider claims Tiger Woods and Vanessa Trump are ‘each other’s ideal type’ after couple’s loved-up display at his lavish 50th birthday bash

Tiger Woods and Vanessa Trump are seemingly as loved-up as ever as the golf icon celebrated his 50th birthday with his high-profile girlfriend by his side.

The 15-time major winner, who turned 50 at the end of last month, toasted the milestone in a lavish bash on Wednesday as a co-celebration of 30 years of his charitable foundation.

READ: How Tiger Woods rumor spreads after PGA Tour legend’;s injury nig

The opulent party, which took place at The Breakers hotel in the billionaire enclave of Palm Beach, Florida, hosted 300 VIP guests who enjoyed a feast that honored the sporting great’s five Masters victories.

And while Woods mingled with the star-studded guest list, he reportedly spent a lot of the night cozied up to his 48-year-old girlfriend.

‘Tiger was with Vanessa but also busy talking to people he knows from the charity,’ a source told People Magazine. 

‘There was some serious partying going down all night by the philanthropists and other high profile guests,’ they continued.

‘They seemed to have a great time,’ the source added.

Meanwhile, another insider weighed in on the romance, claiming that the golfing legend and former wife of Donald Trump Jr. were a match made in heaven.

‘Vanessa and Tiger have a lot in common with each other and with their kids,’ they told the outlet. ‘And each is the other’s ideal type.’

Earlier this week, exclusive Daily Mail photos reveal the recently minted couple with Jon Bon Jovi, who performed an acoustic set ahead of the banquet that honored the sporting great’s five Masters victories.

The love birds, who went public with their romance last March, quietly slipped into the main ballroom for the stunning event, The Daily Mail revealed.

The 15-time major winner chose a classic dark tuxedo look with a red tie and red pocket square, while Vanessa stunned in a slinky black dress and red high heels while carrying a gold clutch bag.

Massive security surrounded the party, with local and state cops flooding hotel corridors.

Meanwhile, Secret Service agents were warily eyeing anyone passing the ballroom doors – behind which Vanessa’s golf protege daughter Kai also was among the revelers.

The 18-year-old presidential granddaughter was seen with a cast on her arm after recent surgery on her wrist.

Woods and his new love chatted with the throng of guests enjoying cocktails and canapes as pop music played at around 6.30pm.

They then slipped out to a nearby small reception room to greet 63-year-old Bon Jovi.

Woods beamed as he had his picture taken with the rock legend, who has a $43million mansion in the exclusive beach town, also home to President Donald Trump. The couple then headed back to mingle.

Just after 7pm, Bon Jovi nipped across the corridor that was guarded by another phalanx of Secret Service agents to head into the ballroom for his acoustic set.

Woods’s combined bash for his TGR Foundation and birthday – which was in December – was given the title RED: Celebrating Legacy.

The color element was down to his signature dress code for the final day of a golf tournament, when he always wears red, a tradition started by his mother, Kultida, who believed it empowered him.

All the guests wore some element of the color as they tucked into the menu of a mix of items from his five Masters Championship dinners.

These included sushi, porterhouse steaks, crab cakes, cheeseburgers, steak and chicken fajitas, stuffed jalapenos, French fries and milkshakes.

The glowing tribute event wound up shortly after 10pm, with revelers flowing out of the ballroom clutching their small black boxes.

Woods and Vanessa began dating in November 2024 after meeting at events at the $38,595-a-year Benjamin School, where both their children attended.

Vanessa married ex-husband Donald Trump Jr. in 2005 and divorced in 2018. They share five children: Kai, Donald III, Tristan, Spencer and Chloe. The divorce was relatively amicable, and both Donald Jr. and his father, President Donald Trump, have put their seals of approval on her relationship with Woods, Daily Mail can reveal.

Woods shares two kids – Sam Alexis and Charlie – with ex-wife Elin Nordegren, whom he married in 2004 and divorced in 2010 after a shocking sex scandal in which he publicly admitted to cheating on her with multiple women during their six-year marriage.

And as Woods’ career winds down after a litany of injuries, it appears he is leaning on his new girlfriend more and more.

‘She came into his life at just the right time,’ a source close to Woods told the Daily Mail. ‘She showed up as he was seriously considering what happens next in his career. She has added so much stability on the home front, and he gushes about her influence in his life.’

Tiger Woods confirmed his relationship with Vanessa Trump in March 2025 via an Instagram post, raising more than a few eyebrows along the way when he declared, “Love is in the air and life is better with you by my side!” The superstar golfer spoke glowingly of his “journey through life” with his new flame before making the obligatory plea for privacy.

As odd as the coupling might seem, it actually makes perfect sense. Both have close ties to President Donald Trump: Woods through golfing events, and Vanessa by virtue of her former marriage to first son Donald Trump Jr. Woods’ children attend the same Palm Beach private school as Vanessa’s daughter, Kai Trump, who’s a promising golfer herself. In fact, the couple is said to have met through social events at the exclusive Benjamin School.

Yet while no one is questioning the sincerity or depth of the couple’s love, they may not be staying together strictly for romantic dinners and cuddles on the backyard hammock. Sources tell the Daily Mail that the champion, who turned 50 in December 2025, is feeling the effects of his age and the physical limitations that come with it.

READ: Why Tiger Woods Needs to Marry Vanessa Trump Soon ‘To Keep

Injuries and surgeries in recent years have clearly limited Woods’ ability to play, and there are rumors he may opt to retire rather than try staging a comeback. If that happens, he may need the emotional support of a loyal partner more than ever. “[Trump] came into his life at just the right time,” explained an insider. “She showed up as he was seriously considering what happens next in his career. She has added so much stability on the home front, and he gushes about her influence in his life.”

Tiger Woods is getting the thumbs-up from important family members

Two prominent members of President Donald Trump’s family have given their blessing to Vanessa Trump and Tiger Woods. When their relationship was first made “Instagram official,” first daughter Ivanka Trump cheered in the comments section, “So happy for you both!” Bettina Anderson, now engaged to Vanessa’s ex, Donald Trump Jr., was equally delighted: “Beautiful couple. So happy for you both,” she wrote. While Don Jr. himself hasn’t publicly commented, sources tell Page Six that he wishes his ex nothing but the best with her new love. The president’s long-time friendship with the Grand Slam champ also factored into Don Jr.’s opinion: “He also knows that his father respects Tiger and how well they get along,” an insider said.

Even more importantly, at least one of Vanessa’s children seems to be on board with her mom’s new beau. Kai Trump accompanied her to the January 15, 2026, gala honoring both Woods’ 50th birthday and the 30th anniversary fundraiser for his TGR Foundation, an initiative that provides STEAM-based educational programs to underserved areas in several cities. Kai, stunning in a red gown, seemed genuinely delighted to be there; at 18, she could easily have begged off going or copped a teen attitude. The fact that she was happily present — and loves golf — seems to bode well for the family.

Woods isn’t hanging up his golf bag just yet, though he’s said he’s still working to get back in shape before he can compete again, as he entered 2026 still slowly recovering from his second back surgery in one year. With the support of both his new girlfriend and the women in her circle, he could enjoy a final season or two before planning a post-tournament future.

Tiger Woods Needs to Marry Vanessa Trump Soon ‘To Keep Her Happy’

Vanessa Trump is allegedly putting pressure on Tiger Woods to propose sooner than later. An insider says Donald Trump Jr.’s ex-wife is ready to see a ring on her finger, but the 50-year-old golfer is still carrying a lot of baggage from his prior marriage to Elin Nordegren given all the mistakes he made. A prior source in June 2025, only a few months after the pair made their relationship public through an Instagram post, said that Woods already had plans to marry Vanessa Trump “fairly soon” at the time, but a proposal has yet to materialize.

READ: Why Greg Norman Puts Rory McIlroy, Tiger Woods on Blast for Nev

Woods worried he won’t “succeed at marriage,” insider says

“It’s no secret that she wants to take things up a notch and have a ring on her finger,” said a source about Vanessa Trump and Tiger Woods to the National Enquirer. “There’s pressure to propose coming down on him for sure.”

However, according to the insider, Woods is allegedly frightened that he’s going to fail his second shot at marriage and still carries a lot of regrets about his extramarital affairs that destroyed his first marriage.

The source explained, “It’s been nearly twenty years since [Tiger] blew his marriage to Elin and to this day, he will admit that was the biggest fumble of his life. He doesn’t talk about it a lot but on the rare occasion he opens up, he admits the regret still weighs on him pretty heavily.”

Compared to Nordegren, who has since married retired NFL tight end Jordan Cameron and has had several children with him, it’s apparently been harder for Woods to move on.

“Tiger hasn’t been able to do the same, at least not until he met Vanessa,” the source continued. “They really seem like a great match.”

“The only question is whether he’ll fully be able to shake his baggage from his divorce. It’s not just regrets over tearing his family apart. He also worries that he won’t be able to succeed at marriage.”

That said, the insider says Tiger would be making a mistake if he doesn’t propose soon. “He’s going to have to face his fears and do it before too long if he’s going to keep her happy.”

In the meantime, Tiger Woods has been advising Kai Trump, Vanessa’s daughter, in her debut on the LPGA Tour.

Vanessa and Kai Trump steal the spotlight at Tiger Woods’ 50th birthday bash

Vanessa Trump and her daughter, Kai, owned the room at Tiger Woods’ 50th birthday bash.

The former daughter-in-law of Donald Trump and her daughter turned heads the minute they stepped into the celeb-packed room, celebrating Woods at the luxury Florida resort The Breakers on Wednesday night.

Although the golf legend turned 50 on December 30, Woods waited to throw an ultra-exclusive celebration worthy of his legacy – one packed with over 300 guests, an acoustic performance by Bon Jovi, and dinner experience inspired by Augusta – to help benefit his TGR foundation.

READ: Tiger Woods offers surprise update on his recovery from seventh b

Guests who made the invite list were instructed to wear a “touch of red,” a powerful nod to Tiger’s infamous “Sunday Red” tradition of wearing red polos during the final round of tournaments.

Vanessa set the tone in a sleek, low-cut black dress paired with statement red heels. Meanwhile, Kai, an aspiring golfer, understood the assignment perfectly, and was dressed to impress in a red, silk mermaid-style gown paired with a cast on her left arm – the result of a recent wrist surgery.

Kai shared two photos from the fete on Instagram Wednesday night, showing off her and her mom’s glam look.

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The night was so meticulously planned that it even had a name, “RED: Celebrating Legacy presented by EY US,” with Ernst and Young stepping up as a presenting sponsor. The event also marked a major milestone, the TGR Foundation’s 30th year of fundraising.

It’s no surprise that Vanessa and her daughter were there to support Tiger. Both share a close bond with the golf legend, ever since Tiger announced in March 2025 that he was dating Vanessa.

At the time, the 82-time PGA Tour winner included two loved-photos with Vanessa in his Instagram announcement, with one showing Donald Trump Jr.’s former wife laying with her head on his shoulder on an outdoor swing.

“Love is in the air and life is better with you by my side! We look forward to our journey through life together. At this time we would appreciate privacy for all those close to our hearts,” Tiger captioned the post.

Unseen Moments of Tiger Woods With Late Earl Woods Surface as GF Vanessa Trump & More React

Tiger Woods has been one of the biggest stars. Yes, that might sound like a cliched sentence, but the truth is, Woods is still equally impactful as he was in his prime. And this is not something that any golfer has been able to pull off. Thus, when such a personality celebrates his 50th birthday, the hype is bound to shoot over the roof. Recently, the TGR Foundation took to their official Instagram handle to celebrate Woods’ birthday. As the sports world celebrated Woods’ legacy, a single photo from his past with his late father captured the attention of fans and family alike.

In one of the snaps, a young Woods can be spotted alongside his late father, Earl Woods. It was a throwback picture from one of Tiger’s birthday celebrations when he was a kid. There was another old picture where the US golfing legend could be seen standing beside his father on a golf course. Alongside these particular snaps, the carousel also featured several activities undertaken by the foundation on the occasion of the legend’s birthday. Woods could also be spotted posing with his family.

JUST IN: “He wants to be perfect”: Tiger Woods’ son Charlie Woods and his

Captioning the post, the foundation wrote on Instagram, “Today we celebrate 50 years of legacy, on and off the golf course.  Happy birthday to our founder, @TigerWoods! His vision, leadership and unwavering belief in the power of education have inspired generations and empowered thousands of students to unlock their potential and bring their dreams to life.”

Soon, with love pouring in, the post gained a significant amount of traction. Notably, Vanessa Trump liked and reshared the same, as she felt proud of her partner.

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Coming to the bond between the late Earl Woods and Tiger, the relationship went well beyond that of a typical father-son relationship. After all, it was his father who inspired the legend to pick up a golf club early on in his life. Throughout his career, Earl Woods constantly motivated and mentored him, shaping Tiger into the champion that he is today. He was so confident in his son that he made a prophecy years in advance.

Back in 1996, when Tiger was just 20 years old, Earl Woods told Sports Illustrated, “Tiger will do more than any other man in history to change the course of humanity. I don’t know exactly what form this will take, but he is the Chosen One.”

Well, surely, the rest is history now. Earl’s prophecy spoke of an impact beyond golf, and decades later, that influence remains undeniable, as proven by his recent win in the Player Impact Program. Calculating the results of the 2024 Player Impact Program, Woods came out as the winner, bagging a whopping $10 million bonus!

Even as the golfing legend is struggling with his health, he stands tall in terms of impact. At 50, Tiger Woods is still the most Googled golfer in all the years of the Player Impact Program. Meanwhile, as the picture of Earl Woods gained traction, fans could not help but comment on the same.

Fans shower love & support for Tiger Woods’ throwback picture with his late father

As soon as the post went viral, fans flocked to the comments section. One fan wished Woods, mentioning how the legend is their favourite golfer. “Happy Birthday to my favorite pga tour golfer tiger woods”, read the comment.

Reflecting on the past, another Instagram user expressed their emotions, saying, “Happy Birthday, Tiger!❤️🥰🏆🥳 Thanks for the many years of great play in Sunday Reds. You are awesome.” Referring to the legend as the Greatest of all time, another netizen commented, “Tiger, my GOAT, and wishing you all the best in your future endeavors.”

Lately, his injuries and surgery have been keeping the star away from the competitive realm. But while Woods looks forward to making a comeback, his fans, too, are waiting with bated breath. One such fan wrote on his birthday post, “Look out @pgatourchampions Tiger’s coming! Can’t wait to watch him.”

Echoing the same thoughts, another fan stated, “Happy 50th Tiger!!! 🐯🐐 wishing you the best of health and your return to tournament golf ⛳️ 💯💪.” Thus, with Tiger Woods’ impact still unquestioned, fans are eagerly waiting for an update on when he will be coming back to professional golf again.