Photo Of Don Jr. And His Fiancée At Trump Tower Party Confirms One Shady Thing

So much can change in a year. Barely two weeks before Christmas 2024, Donald Trump Jr. confirmed what everyone already knew: He and Kimberly Guilfoyle had split up. President Donald Trump's namesake eldest son was engaged to the former Fox News host for years, but the couple's reluctance to announce wedding plans understandably left fans highly suspicious. Then came the tabloid photos of Don Jr. stepping out in secret with his new lady love, Palm Beach socialite Bettina Anderson, and from there it was just a matter of time before the announcement was made.

Now Christmas 2025 is close at hand, and Don Jr. has already taken his relationship with Anderson to the next level. Not only has the happy couple enjoyed several romantic weekend getaways together, but Anderson has also hung out with Don Jr.'s five children and his sister, Ivanka Trump. When your boyfriend wants you to meet the family, you know it's serious. But surprisingly, the news hasn't entirely reached all of Trumpworld. Over the weekend of December 13, the couple flew to New York to attend the annual Christmas party at Trump Tower, and shared a couple of sweet shots posing in front of the Christmas tree to their respective Instagram Stories. 

Don Jr & his girlfriend Bettina at the Trump Tower Christmas party ❤️🎄 pic.twitter.com/q8rTzhf12n

— Keeping Up With The Trumps (@KUWTTRUMPS) December 14, 2025

Don Jr. and Anderson have notably avoided posting couples photos to their permanent feeds thus far. As such, on X, formerly known as Twitter, a Trump fan posted a screenshot of the now-expired pics, and the sight shocked folks who hadn't been following the whole soap opera. "Where is Kimberly??" cried one such user. Others offered similar comments, but with much less complimentary language. One wished Guilfoyle well in her new role as U.S. ambassador to Greece, admitting, "Still can't get used to him without Kim. I hope she finds some really attractive Greek husband."

The reaction to the loved-up Christmas portrait of Donald Trump Jr. and Bettina Anderson was surprisingly mixed. Some users on X heartily approved, opining that the model seems classier and more stylish than Kimberly Guilfoyle, whose fashion fails are often the target of gasps and snarks. The word "upgrade" was used repeatedly. Quite a few commenters also noted Anderson's more natural appearance, which stood out among the so-called "Mar-a-Lago face" so often seen on women in President Donald Trump's sphere (Guilfoyle is widely considered to be one of the biggest victims of the trend). "Very pretty. I hope [Anderson] doesn't go with the big lips and all the dark makeup," one commenter wrote. Others were highly doubtful that the romance would go the distance. "He'll have a new one for the Easter festivities," yawned a skeptic. Even more surprising, though, were the backseat critics who got nostalgic for his first wife. 

Even though there were plenty of signs that Don Jr. and Vanessa Trump's marriage was doomed from the start, the optimists still kept their fingers crossed for a second chance at love. One put it bluntly: "Donnie Boy, You can do better man. Stop playing. Enough. The mother of your children @MrsVanessaTrump is the most stunning and classiest mom. God gave her to you. I hope and pray you reconcile for the sake of your kids." Sorry to say, those prayers seem destined to go unanswered. Vanessa Trump is now in a relationship with golf legend Tiger Woods, and insiders reckon she scored big with him. Whatever occurs with either Don Jr. or Vanessa's new loves, it's clear that Guilfoyle is out of the picture.