The chatter about Tiger Woods’ splashy reveal that he’s dating Vanessa Trump has included plenty of comments about Donald Trump Jr. On March 23, Woods made his relationship with Vanessa Instagram official with a post that included a snap of the golfer standing beside his new girlfriend and a photo of the couple snuggling together. “Love is in the air and life is better with you by my side! We look forward to our journey through life together,” Woods wrote in the caption. Prior to this relationship, Vanessa had divorced Don Jr. in 2018 after 12 years of marriage, but the pair stayed on amicable terms as they co-parented their children. Ivanka Trump noticed Woods’ hard-launch relationship post and showed up in the comments to support her former sister-in-law. “So happy for you both!” Ivanka replied. Not only did his sister weigh in, but so did Donnie’s girlfriend.
Bettina Anderson, whose relationship with Don Jr. had only been made Instagram official the previous month, wrote in response to her boyfriend’s ex-wife’s new boyfriend’s relationship announcement, “Beautiful couple. So happy for you both.” Followers noticed the reply, and a mini-debate ensued. One Instagram user questioned if Anderson was actually happy for Vanessa, while others pointed out that Don has a healthy relationship with the mother of his children. To further complicate matters, Don Jr.’s ex-girlfriend, Kimberly Guilfoyle, left a like on the Vanessa-Woods post.
Before they took their relationship public, a source told People that Don Jr. was “cool” with the news that his ex-wife was dating Woods. This all unfolded while the first son was juggling his own messy love life.
Donald Trump Jr. did not make a clean break with Kimberly Guilfoyle
After news of his break up with Kimberly Guilfoyle broke in December 2024, Donald Trump Jr. made his relationship with Bettina Anderson Instagram official in February. Junior attended the Super Bowl with Donald Trump and uploaded an Instagram carousel after the big game. It included photos with his kids and pics of Anderson posing with the family.
It should be noted that the first few slides were of Don Jr. and his family, and it was not until later in the post that he slid in the snaps with his new girlfriend. Some followers were displeased to see him make the romance official, considering he had just been dating Guilfoyle. “Sure are asking your children to shift gears pretty quickly, she’s a social climber and is just waiting for a book deal,” one Instagram user commented. A month after posting the new girlfriend to his timeline, Don Jr. and Anderson packed on the PDA when they attended the amfAR gala in Palm Beach. Clearly, Donnie had moved on, but Guilfoyle was still in his orbit.
Don Jr.’s past and present love lives collided when he brought Anderson along for inauguration festivities in January. Guilfoyle, a longtime member of Team Trump, was also in attendance. “Kim is still very fond of Don, and kept a watchful eye out,” a source told People about the trio crossing paths. While seemingly amicable, the split from Guilfoyle was reportedly anything but a clean break. “[Guilfoyle] has every intention of maintaining a relationship with [Don Jr.],” a source told Page Six after the inauguration run-in.
