Tiger Woods' Reported Romance With Don Jr.'s Ex-Wife Leaks Out (& It Explains So Much)

There's a new member of the Trump family inner circle and he's taking the world by storm. When Tiger Woods made an appearance at the White House to be honored by President Donald Trump, the mysterious relationship between Woods and Trump resurfaced. Many assumed Trump just wanted to give the Presidential Medal of Honor to a golf player, as that is his favorite sport, but with new information about who Woods is currently dating, it casts a very different light on some of his recent actions. According to the Daily Mail, it seems that Woods and Vanessa Trump — mother of Donald's favorite granddaughter, Kai Trump, and ex-wife of Donald Trump Jr. — have been secretly dating since at least Thanksgiving 2024.

Vanessa and Woods being an item certainly puts some of the pro golfer's recent actions into perspective. Everyone was scratching their heads at the timing of Woods' appearance alongside Kai at a golf tournament after suffering the tragic loss of his mother, Kultida. But now that the cat's out of the bag, it makes so much more sense for Woods to have accompanied Kai — and is a good indication that he has Kai's seal of approval for dating her mom.

While the two live close to each other and have children similar in both age and interests, there are still several good reasons Vanessa and Woods might have kept their dating life private, many of which involve the scandalous dating life of Don Jr. (although, there's plenty that Tiger's exes have said about him, as well).

While there are many things working in Tiger Woods and Vanessa Trump's favor — Woods' kids live a lavish life that allows them to attend the same school as Kai Trump and both his son Charlie and Kai have ambitions of becoming professional golfers — there's still a giant red flag in the couple's way. Donald Trump Jr., whom Vanessa divorced in 2018 for cheating on her with Kimberly Guilfyole (who has since been kicked to the curb), has a way of making Vanessa's dating life difficult.

For reasons Vanessa has never fully divulged, she's avoided taking on any major romances since her split from Don Jr. The same cannot be said for her ex-husband, who has now moved on from Guilfoyle with the much younger Bettina Anderson. This seemingly caused a bit of a rift between Vanessa and Don Jr., as she and Anderson were friends before Don Jr. began dating her. 

Running in the same Palm Beach, Florida circles, Vanessa and Anderson rubbed shoulders often, especially when Anderson helped host a fundraiser for Donald Trump's election campaign in October 2024. However, when it was revealed that Don Jr. and Anderson were officially an item, Vanessa had some hard feelings about it. It's always a bit tacky to date your ex's friends, Don. However, sources divulged to the Daily Mail that since Vanessa and Woods started dating, Anderson decided there's no need for animosity. Wishing all parties the best of luck with that.