Don Junior isn't just dating anymore. He's engaged.
If you haven't been keeping up with the Mar-a-Lago social circuit lately, the news might come as a bit of a shock. For years, the image of Donald Trump Jr. and Kimberly Guilfoyle as the ultimate MAGA power couple seemed set in stone. They were the fiery duo on the campaign trail, the loud voices at every rally, and the pair everyone expected to see walk down the aisle.
But things changed. Fast.
The New Chapter: Who is Don Junior Dating Now?
The short answer? Bettina Anderson.
She’s a Palm Beach socialite, a model, and someone who moves in very different circles than the high-octane political world of Kimberly Guilfoyle. The engagement became official on December 15, 2025, when none other than President Donald Trump himself announced it during a Christmas reception at the White House.
It was a classic Trump move. Big stage, plenty of witnesses, and a video that immediately went viral thanks to a post by Laura Loomer. Don Jr. stood at the podium, looking genuinely happy—and maybe a little relieved—as he thanked Bettina for saying "yes."
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He called it a "big win for the end of the year."
Bettina, for her part, seems to be embracing the spotlight. She’s the daughter of philanthropists Harry Loy Anderson Jr. and Inger Anderson. If you follow the Palm Beach scene, you’ve probably seen her name linked to the Hope for Depression Research Foundation or Project Paradise. She’s polished. She’s "Waspy," as some insiders have put it. And according to sources close to the family, she’s exactly the kind of partner Don Jr. felt would impress his father.
The Quiet End of the Kimberly Guilfoyle Era
So, what happened to Kimberly? Honestly, it was a slow burn that ended in a quiet exit.
The two had been engaged since New Year’s Eve 2020, but the wedding never actually materialized. By late 2024, rumors were everywhere. People noticed they weren't appearing together as often. Then came those photos of Don Jr. holding hands with Bettina in Palm Beach around December 2024.
At the time, the split hadn't been made official. It was messy. Or at least, it looked messy from the outside.
Insiders told Page Six that the couple had been bickering at Mar-a-Lago for months. Nothing explosive, just the kind of public friction that suggests a relationship has run its course. While they were still technically together, Don Jr. was already being spotted on brunch dates and birthday dinners with Bettina.
The "Ambassador" Exit Strategy
One of the most fascinating parts of this breakup was how it was handled politically. In December 2024, President-elect Trump nominated Kimberly Guilfoyle to be the U.S. Ambassador to Greece.
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Many saw this as a graceful way to move her "out of the area" while keeping her in the fold. She was confirmed by the Senate in September 2025 and officially moved to Athens in November.
It’s a long way from Florida.
Guilfoyle has since broken her silence. In an interview with The New York Times in early January 2026, she said she was "happy for Don" and wished him the best. It’s the professional answer, but reports suggest the transition wasn’t easy. She still co-owns a $9.7 million mansion in Jupiter, Florida, with Don Jr., though he is reportedly living in Bettina’s townhouse now.
Why the Switch to Bettina Anderson Matters
Relationships in this family are rarely just about romance; they’re about the brand.
Kimberly was the "sledgehammer." She was loud, aggressive, and 100% focused on the political movement. Bettina represents a shift toward a different kind of image. Some have compared her to Melania—a model with a more reserved, aristocratic vibe.
- Background: Bettina is a staple of the Florida high-society charity circuit.
- Connection: She and Don Jr. reportedly started dating around mid-2024, even while the public still thought he was with Kimberly.
- Family Ties: She accompanied Don Jr. to the 2025 inauguration and has been a frequent guest at Mar-a-Lago events.
The Trump family seems to have embraced her quickly. Even Vanessa Trump, Don Jr.'s first wife, has been vocal in the past about supporting his choices, provided they focus on the five kids they share: Kai, Donald III, Tristan, Spencer, and Chloe.
Actionable Insights for the Curious
If you're following this story for more than just the gossip, there are a few things to keep an eye on as we move through 2026:
- The Jupiter Mansion: Watch the real estate listings. Until that $9.7 million property is sold or transferred, Don Jr. and Kimberly are still legally and financially tied together.
- The Wedding Date: With the engagement official as of late 2025, expect a high-profile wedding at Mar-a-Lago sometime this year. It will likely be a massive social event for the Palm Beach elite.
- Kimberly’s New Life: Guilfoyle is currently in Athens. Her social life there is already making headlines, and she has joked about looking for a "new husband" in Greece.
Don Jr. has a history of long relationships and long engagements. Whether this one makes it to the altar faster than the last remains to be seen, but for now, the "who is Don Junior dating" question has a very definitive, diamond-encrusted answer.
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Keep an eye on social media updates from Kai Trump—the 18-year-old often provides the most candid glimpses into the family's internal dynamics.