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.

Fifteen-time major champion Tiger Woods announced his relationship with Vanessa Trump in March, and since then, the couple has aimed to keep their romance out of the public eye

Tiger Woods and Vanessa Trump caught the attention of many, including those closest to them, when they announced their relationship in March

Woods, who is currently recovering from an Achilles injury that has ruled him out of PGA Tour action, went public with Vanessa via a statement on social media earlier this year. “Love is in the air, and life is better with you by my side!” Woods posted on X and Instagram.

“We look forward to our journey through life together. At this time, we would appreciate privacy for all those close to our hearts,” he added, accompanied by two loved-up photos.

Vannessa had previously been married to the son of the President of the United States, Donald Trump Jr. Woods, too, is known to share a good relationship with the Trump family, having recently played golf with Donald Sr. and negotiating the PGA Tour’s ongoing peace talks with LIV Golf with the President.

In the wake of the relationship announcement, the Trump and Woods families had their say on Woods’ and Vanessa’s love interest.

Donald Trump Sr.

The President revealed at the end of March that the 82-time PGA Tour winner had contacted him about his relationship with his ex-daughter-in-law, and the Republican gave his blessing. “I love Tiger and I love Vanessa,” Trump declared at the White House

“Tiger actually called me a few months ago. I have a very special relationship with Tiger. He’s a fanatic guy. I said Tiger that’s good. I’m very happy for both… “They (Donald Jr. and Vanessa) had a great relationship.

“I happen to think the relationship with my son was hurt very badly with the witch hunt. ‘Russia, Russia, Russia’. All the c— they put Don through. Vanessa and Don have a great relationship. Five great children. They broke up quite a while ago, which to me was very sad.”

Donald Trump Jr.

Despite their past marriage, Trump Jr is seemingly happy with his ex-wife dating the 15-time major champion. In the wake of the romance going public, with a report from PEOPLE claiming that the son of the President is “cool” with Vanessa’s new love interest.

Don and Vanessa have five children together, including Kai Trump, who is looking to forge her own career in golf. Both Kai and Charlei Woods, the son of Tiger, recently competed in one of the most prestigious junior events in the sport at the Junior Invitational at Sage Valley.

Sam and Charlie Woods

Along with Charlie, Woods has a daughter named Sam, who is pursuing a career in soccer rather than on the golf course. Both Woods’ kids appear happy with their new stepmother, after a Daily Mail source claimed: “She likes the kids; they like her.”

Sam and Charlie’s mom, Elin Nordegren, split from the golfing great back in 2010, but the pair appear to share a mutual relationship amid their relationship with their kids. Providing an insight into Nordegren’s reaction to her ex-husband’s new relationship, the insider added: “There was really no reason for any drama with Elin

“It was more of a call, so she didn’t learn about it in the news. “Tiger knew it was going to get out eventually, so he had to make the phone call to Elin before his love life ended up in the newspapers again. He’s made this call before about other women – but never like this…

“Her response at first was like, ‘Seriously? A Trump? For real?’ She was more amused than anything. But she really quickly just accepted it.”

Vanessa Trump Steps Into the Spotlight With Tiger Woods by Her Side

Vanessa Trump is back in the headlines—but not for politics or past headlines. This time, it’s about new beginnings, as she and golf icon Tiger Woods have officially confirmed they’re a couple.

The surprising romance was revealed on Instagram with both Vanessa and Tiger posting affectionate photos. Vanessa, wearing a relaxed smile, looked every bit at ease with Tiger by her side. Her caption? Subtle yet telling. His? A little more poetic: “Love is in the air and life is better with you by my side.”

Behind the Romance: How It Started

Insiders say the two have been quietly dating since November 2024. Their connection began through shared social circles in Palm Beach—and more unexpectedly, through their kids. Vanessa’s son, Kai Trump, and Tiger’s son, Charlie Woods, attend the same prestigious Florida school and are both junior golfers. School drop-offs and weekend tournaments soon turned into something more.

Donald Trump Reacts—And He’s Totally Fine With It

In a rare show of chill, Donald Trump gave the relationship his blessing. “Tiger actually called me a few months ago. I love Tiger, and I love Vanessa. Let them both be happy,” he said. No drama, no tabloid blow-up—just support from the former President and former father-in-law.

Even Ivanka Trump chimed in, commenting “So happy for you both” on Vanessa’s post with heart emojis. So far, the Trump family seems aligned.

Vanessa’s Journey Since Her Divorce

Vanessa was married to Donald Trump Jr. for 13 years, and the couple shares five children. Since their split, she has largely kept out of the public eye. But her early years were anything but low-key—Vanessa had a short modeling career and was once linked to Leonardo DiCaprio and even a Saudi prince.

This new relationship with Tiger marks a return to public attention—but on her own terms.

Tiger’s Turn at a Fresh Start

Tiger Woods, of course, has had his share of public relationship drama. After his 2010 split from Elin Nordegren, he laid low romantically—until now. Sources close to him say Vanessa brings a grounded energy that he hasn’t had in years.

The two live near each other in Palm Beach and have reportedly been spending plenty of time together—from quiet dinners to family outings.

Is It Serious?

From the outside, it sure looks like it. This wasn’t a leaked photo or an accidental paparazzi shot—it was a coordinated, public reveal. Sources say they’ve been integrating their families and are committed to making it work.

And let’s be honest—when Donald Trump is already giving you a thumbs up, that’s a pretty strong start in Trump-world.

Fans React: Cheers, Shock, and Everything In Between

The internet, as always, had thoughts. While some are thrilled to see Vanessa finding love again, others are surprised by the unexpected match. One viral comment on X (formerly Twitter) summed it up: “Vanessa Trump and Tiger Woods? That’s the crossover I didn’t see coming in 2025.”

But Vanessa seems unfazed. For now, she’s stepping into the spotlight on her own terms—with Tiger by her side, not in his shadow.