Tiger Woods is going strong with Vanessa Trump, a source exclusively tells In Touch the golf legend is still haunted by the mistakes he made in his womanizing heyday and all he can do now is vow to never to let the past repeat itself. 

“Tiger has never completely forgiven himself for what he put Elin [Nordegren] through, he’s still carrying a lot of shame and guilt for the pain he caused her, not to mention the humiliation they both suffered,” the insider says.” 

“It was such a global scandal and even though it’s been close to twenty years since it all happened, people still judge him for it, and he knows that,” the source adds. 

In 2009, the 82-time PGA Tour champ, 49, watched his five-year marriage to the former Swedish model, 45, go up in flames as outrageous details about his sex addiction and infidelity came to light, starting with Elin discovering her husband’s affair with VIP event organizer Rachel Uchitel after going through his phone. In the dramatic scenes that followed, Tiger locked himself in the bathroom of his mansion before attempting to flee in his car and hitting a fire hydrant. Scores of other women, including models, Playboy Pinup Girls and porn stars, came forward in the following weeks to dish about their liaisons with the pro golfer.

What likely be the most publicly humiliating implosion of any marriage ended with Ellen nabbing $100 million from the sports star in their settlement. She eventually settled down with NFLer Jordan Cameron and had three kids. Tiger, too, has moved on. First with a string of women similarly blonde and tall as his ex wife and most mistresses, including Olympic ski racer Lindsay Vonn and stylist business owner Kristin Smith. The latter relationship also crashed and burned after Kristin discovered her boyfriend with the girl he would date next, Erica Herman.

“Kristin suspected it, but he would always deny it by belittling Erica,” a different source told Radar of Tiger’s infidelity. “Kristin eventually caught them together. It was a big mess.”

He’s now dating Donald Trump Jr.’s ex wife, Vanessa, 47, with whom the once-shamed lothario is “madly in love,” the source adds. With his undignified romantic history front and center, the two seem to be moving past all of the drama of his previous relationships. They confirmed their relationship in March 2025 and ever since, the insider says Tiger’s been “totally devoted to her.” 

Still, with a philandering history as rich and textured as the PGA icon’s, there’s still going to be some lingering mistrust, even if Vanessa, 47, herself has full faith in her new beau. “That doesn’t mean her family and friends aren’t going to question whether he’s really changed, or at least that’s Tiger’s big fear,” the insider adds. 

“It’s this elephant in the room that he wants to address, but what can he really say? He’d do anything to erase his past because he feels like people will always be suspicious of him, it torments him.”