It’s no secret that Tiger Woods has become Donald Trump’s unlikely BFF (much to Elon Musk’s dismay, probably), but no one could have predicted that he would be romantically involved with a Trump — or at least a former one. In case you haven’t heard, he and Vanessa Trump, Donald Trump Jr.’s ex-wife, are apparently head over heels in love, and while MAGA land might be cheering, the rest of us are side-eyeing and wondering if this is really going to last.
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Rumors of Woods and Vanessa dating circulated in March 2025, roughly a month before they hinted that they were a couple. At the time, the Daily Mail revealed that the two had actually been seeing each other since late 2024. “Tiger and Vanessa have been seeing each other since just before Thanksgiving. She comes to his place on Jupiter Island. They’re not living together,” a source dished. “They just love hanging out, having dinner and schmoozing together. They’re sticking close to home, have decided not to make it a thing and go out in public. Not just yet anyway.” But the secret didn’t stay secret for long, with Woods finding himself hard-launching their romance online. “Love is in the air and life is better with you by my side!” he wrote on Instagram, along with pictures of them canoodling. “We look forward to our journey through life together.”
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Sweet? Absolutely, although it’s kind of a left-field move — even for the lover boy who is Woods. And while we’re not here to rain on anyone’s parade, let’s not pretend that their newfound romance is a sure thing just yet. Even some experts seem to think so. After all, Woods’ romantic history is peppered with one too many red flags, and Vanessa’s past is not exactly scandal-free, either.
Tiger’s friends apparently don’t like Vanessa
You technically don’t need your friends’ blessing to date someone you fancy — especially if you’re someone like Tiger Woods. But that doesn’t mean their opinions don’t matter, particularly when they’re reportedly questioning your latest flame. Rumor has it that Woods’ inner circle isn’t exactly thrilled about his budding romance with Vanessa Trump, and they’re already bracing themselves for what they think is an inevitable messy implosion.
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According to Radar, Woods’ buddies are concerned he’s jumping into something he’s not ready for — emotionally and physically. “Tiger is in a very vulnerable state right now,” an insider dished to the outlet. “The last few years have been incredibly tough. And Vanessa’s a real dynamo. She lives a very fast-paced lifestyle and there are concerns he won’t be able to keep up with her.”
But the red flags don’t stop there. The source said that there’s also concern about the athlete’s health, considering that he’s been dealing with a string of injuries since 2021. And while Vanessa is apparently happy tending to him now, his friends are questioning whether that’s just new-relationship energy taking over. “Tiger’s not some old man who just sits around moping all day, but he does have a fairly low-key life. And Vanessa’s known to be a real jet-setter,” the insider added. “She’s not someone who’s going to stick around if she’s not finding things exciting. Everyone’s wondering how long it will be before she drops him like a hot rock.”
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According to an expert, Tiger’s history of cheating can pose a problem
Tiger Woods may have a legendary golf career, but his dating history has been packed with scandals. While married to Elin Nordegren, he famously admitted to cheating on her with multiple women — and even went as far as entering rehab for sex addiction. In an exclusive interview with Nicki Swift, Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, dished that while Woods’ intentions with Vanessa Trump appear to be clean, his cheating past may eventually haunt their relationship.
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“While I don’t always subscribe to the saying ‘once a cheater, always a cheater,’ I do think in this case, sadly, it will always be the backdrop,” she explained. “There are one-time cheaters, and then there are players. While Tiger Woods isn’t exactly a player, he is not a one-time cheater. Whatever his issue is, it is so pervasive that I don’t think he would ever entirely quit cheating.” In fact, Trombetti even labeled Woods as “one of the five types of guys you should run from because this is a fatal flaw.”
To be fair, his subsequent romances with Lindsey Vonn and Erica Herman didn’t blow up over cheating — or at least not that we know of. “He can use them as examples of relationships without issues involving betrayal of trust and cheating which can help build trust that he is a changed man,” Trombetti added. “But it can be a lingering problem. I can’t imagine that not always being in the back of their mind holding a woman back in a relationship at times.” Still, per the Daily Mail, Vanessa is “unworried” about Woods’ past, so whether his history will affect their relationship remains to be seen.
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And so is their relationship being under the spotlight
Tiger Woods and Vanessa Trump knew what they were getting into. Both have long been public figures and part of high-profile romances, so they likely knew that stepping into another one would never be a quiet affair. But while they’re used to the attention, Susan Trombetti notes that it will still likely affect their relationship dynamic.
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“Being in the public eye is a stressor. If they want to put it behind them, it won’t be possible. The public never forgets and they will always be scrutinizing him and any relationship. He will never live this down,” she exclusively told Nicki Swift, although she noted Vanessa may handle the chaos better than Woods. “I don’t think outside scrutiny is going to have much of an impact on his relationship with Vanessa Trump. She is used to dealing with the press and the public, the same way Lindsey Vonn was used to it. I think they should keep their heads down, enjoy the relationship, ignore the chatter, and just say it’s in the past even though the rest of us remember.” And if they intend on staying together for the long haul, Trombetti suggests that they ignore what the tabloids say as early as now and trust no one but each other.
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As for the reason why he went public in the first place? A former staff member told the Daily Mail that he just wanted to get it over with. “I know that Tiger didn’t want to share the news. But now that he has, there has to be some relief. Now he can just go and live his life,” they said. At least he knows how to get ahead of controversy now!
Their supposed insistence on keeping things ‘casual’ is suspicious, too
While Tiger Woods already used the L-word in his hard launch with Vanessa Trump, sources say that the true nature of their relationship is anything but — at least as of this writing. Shortly before they became public, insiders told People that their relationship is “very casual” and that Vanessa is not exactly the type to go all in right off the bat.
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“Vanessa has always gone for guys who are either well known or have something big going for them,” the source shared, adding that she is also not the type to publicize a relationship if she can help it. After all, aside from her marriage with Donald Jr., she was also reportedly involved with the likes of Leonardo DiCaprio. “She is comfortable with that, but she’s not a woman who wants to be in the limelight. She is not a shrinking violet but is discreet and smart and a good mother,” the source added. “That has come first in her life.”
Will they make it past all these red flags? That’s TBD for now, but at least there are a lot of people in their corner, with Donald Trump surprisingly being one of their top fanboys. Who would have thought? “I love Tiger and I love Vanessa,” he told reporters at the White House, adding that Woods even delivered the news to him personally. “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,” the president dished. “Let them both be happy. They’re both great.”
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