All The Signs Vanessa Trump And Tiger Woods' Relationship Will Never Last

Amid rampant dating speculation, Vanessa Trump and Tiger Woods officially announced their relationship on March 23, 2025 — while asking for privacy. "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," the pro-golfer wrote alongside two photos of himself and President Donald Trump's former daughter-in-law on X, formerly known as Twitter.

But their request for privacy while simultaneously telling the world they were dating wasn't lost on social media users. "One of the most confusing captions of all-time," one person tweeted. "You ask for privacy while posting to your 6 million followers," another X user pointed out, alongside a crying laughing emoji.

Requesting privacy amid such a public declaration could be a red flag, as it suggests Woods may be confused by what he wants. Does he really want to keep his and Vanessa's relationship out of the public eye? Or does he want to openly share their romance across social media? There's nothing wrong with either option, but if the golfer is sharing such mixed messages publicly, it's not out of line to wonder if he may be doing the same with Vanessa behind the scenes. And underdeveloped communication skills could be a sign their relationship won't last.

Tiger Woods' history of infidelity is no secret, as his indiscretions while married to Elin Nordegren, who's totally transformed since their divorce, are well-documented. Though the sports superstar never officially confirmed how many women he'd been intimate with while married to the mother of his children, at least 11 women came forward in 2009. Of course, there are occasions where a cheater has truly learned their lesson and has worked hard to not make the same mistake, but Woods having so many very public cheating incidents in his past isn't exactly a green flag. Daily Mail even purported that Woods also stepped out on ex-girlfriend Lindsay Vonn before they split in 2015, but neither confirmed the report.

Nicole Moore, celebrity relationship expert and host of the "Love Works" podcast, previously told Women.com that cheating can point to a deeper problem. "Typically, people cheat due to unresolved emotional issues within themselves or due to inability to communicate and operate with integrity in a relationship," she said, in reference to the red flags Ryan Reynolds and Blake Lively have exhibited. She added, "They can often carry those issues into the next relationship."

In 2010, The Guardian reported Woods had supposedly sought treatment for sex addiction. If true, his cheating past may not be so much of an issue with Vanessa, as he should be equipped with the tools to remain faithful. However, if he hasn't or isn't willing to seek help, it could be the root of potentially serious relationship issues.

When Vanessa Trump split with Donald Trump Jr., a source told Page Six she was uncomfortable with the intense attention thrust on her and her family thanks to Donald Trump's presidency. "Vanessa is by nature is a very low-key person, and she is uncomfortable with the attention her family is getting now the Trumps are on the world stage," they said. "She is also worried for her kids."

Vanessa embarked on a quieter life after finalizing her divorce from Don Jr. (who went on to show some warning signs of his own with his ex, Kimberly Guilfoyle) in 2019. Though Vanessa has a public Instagram, she only has seven posts at the time of writing that mainly show her children practicing golf, and she isn't often seen at her ex's famous family's events.

The problem? Though Tiger Woods doesn't command quite as much attention as the president of the United States and his family, his romance with Vanessa won't go under the radar — and that could be a sign their relationship may not last. At the time of writing, his relationship announcement has over 90,000 likes on X, with a further over 371,000 on Instagram. So, if Vanessa is hoping for a low-key, private relationship and a quieter life away from the spotlight, she's unlikely to find it with the most famous golfer in the world. 

Long-distance relationships can be hard enough, but throw in a huge amount of media attention and blended families and it only gets more complicated. Though Vanessa Trump and Tiger Woods are thought to live around 20-minutes' drive apart in Florida, they won't always be so close. Woods travels the world as a professional golfer and is away from the Sunshine State on a regular basis. Seeing as Vanessa shares five children with her former husband Donald Trump Jr., she may not have the ability to drop her life in Florida and hop on a jet for Woods' tournaments (and she may not want to, either).

That could be a problem for their relationship, as not enough time together was blamed for Vanessa and Don Jr.'s split. "It is getting harder to resolve their issues. He's never there," a source told Page Six in 2018. Distance and busy schedules were also factors when Woods broke up with his ex-girlfriend, alpine ski racer Lindsay Vonn. Writing on Facebook about their breakup, Vonn shared, "Unfortunately, we both lead incredibly hectic lives that force us to spend a majority of our time apart." And we can't see things being much different between Woods and Vanessa. That could lead to resentment and a lack of time to truly bond, which aren't signs of a healthy relationship set to go the distance.