Tiger Woods may be head over heels for Vanessa Trump, but the 15-time major champion is reportedly dragging his feet when it comes to popping the question. According to insiders, the scars from his bitter divorce from Elin Nordegren are still fresh enough to make him pause before walking down the aisle again.
Just last week, Page Six reported that Woods and Trump are "very serious" about each other, having gone public with their romance back in March 2025. They've even talked about marriage, but a proposal isn't exactly imminent. "They're very serious about each other and absolutely see a future together," a source told Page Six. "Marriage is something they've talked about, but that doesn't mean a proposal is necessarily around the corner. Going through difficult times together has brought them closer and shown them that they can count on one another. It's one thing to enjoy the good times together, but they've also seen how the other person handles things when life gets difficult."
But according to Globe Magazine, the golf legend's past is casting a long shadow over his future with Trump. Woods' marriage to Nordegren imploded in 2010 after allegations of infidelity surfaced, leading to a $100 million settlement. That painful chapter has left him wary of repeating the same mistakes. "Tiger adores Vanessa. But he's also got a lot of baggage from his first marriage," an insider told Globe Magazine. "His breakup from Elin was horrible. Tiger has so many regrets, and when you get right down to it, that's really what's holding him back from proposing to Vanessa. He's afraid he's going to fail again."
The couple has certainly faced their share of trials. Earlier this year, Woods was arrested in Florida on suspicion of DUI with property damage, and Trump stood by his side. As part of his plea deal, his driving privileges were suspended for five years. Meanwhile, Trump herself battled cancer and has thankfully been declared cancer-free. These shared hardships have reportedly strengthened their bond, proving they can lean on each other when the going gets tough.
Woods has also been focusing on his health, taking a step back from the spotlight to prioritize his well-being and support Trump through her treatment. The couple's resilience has impressed those close to them, but the question remains: will Woods overcome his fears and take the next step?
Fans are hopeful that 2027 might bring a new chapter for the couple. With Woods showing signs of a potential comeback, as seen in his fresh look sparking hope for 2026, the future looks bright on the course. Off the course, only time will tell if he can let go of the past and embrace a new beginning with Trump.
As the world watches, one thing is certain: love isn't the issue for Woods and Trump. It's the baggage that comes with it. Whether he can overcome those regrets and finally propose remains to be seen, but for now, the golf icon is taking it one day at a time.
