If you’ve been following the MAGA orbit lately, you’ve probably noticed the scenery has changed. For years, Kimberly Guilfoyle was the constant presence at Donald Trump Jr.’s side, her high-energy speeches and "The best is yet to come!" catchphrase becoming a staple of the campaign trail. But things move fast in Florida. Honestly, the question of who is Trump Jr dating has a very different answer today than it did just a short while ago.
The news is official now. Donald Trump Jr. is engaged to Bettina Anderson. It wasn't a leaked tabloid rumor or a grainy paparazzi shot that confirmed it this time. Instead, his father, President Donald Trump, made the announcement himself during a White House Christmas party on December 15, 2025. Don Jr. followed up by calling the engagement a "big win for the end of the year." It’s a massive shift for the Trump family dynamic, especially considering how long Guilfoyle was in the picture.
Meet Bettina Anderson: The Woman Who Captured the Eldest Trump Son
So, who exactly is the new woman in the inner circle? Bettina Anderson isn't a political firebrand or a cable news host. She’s a 39-year-old Palm Beach socialite and model. While Guilfoyle was known for her aggressive, booming stage presence, Anderson comes from a world of old-money Florida philanthropy and high-fashion galas.
She is the daughter of the late Harry Loy Anderson Jr., a heavyweight in the banking and insurance world.
She’s got the pedigree to match the Mar-a-Lago scene. She graduated from Columbia University with a degree in art history and has spent years as a local influencer and model in Palm Beach. If you look at her Instagram, it's less about political rants and more about luxury jewelry shoots for Hamilton Jewelers and conservation efforts. She’s heavily involved with The Paradise Fund, a nonprofit she co-founded with her brothers to help with disaster relief and environmental causes.
Basically, she’s a different vibe entirely.
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Why the sudden change from Kimberly Guilfoyle?
The transition was, well, a bit messy behind the scenes. People first started asking who is Trump Jr dating back in August 2024 when photos surfaced of Don Jr. and Bettina having brunch together in Palm Beach. At the time, he was technically still engaged to Guilfoyle. They had been living together in a $9.7 million mansion in Jupiter, Florida.
But by late 2024, the writing was on the wall.
Rumors swirled that the President himself preferred Anderson’s more "understated" and "waspy" look compared to Guilfoyle’s often-criticized "grandstanding" style. According to some sources, the elder Trump felt Guilfoyle was trying to put too much of the MAGA spotlight on herself.
The Current Relationship Status in 2026
Fast forward to January 2026, and the couple is seemingly inseparable. They’ve been spotted everywhere from the FIFA Club World Cup to family trips in Scotland. Anderson even accompanied Don Jr. to the presidential inauguration in January 2025.
She’s managed to do what few outsiders do: win over the family.
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Sources close to the Trumps suggest that Bettina has "mellowed out" and learned the unspoken rules of the family—namely, looking great and letting the Trump name take center stage. Don Jr. reportedly threw her a massive birthday party recently, and word on the street is that he’s essentially moved into her Palm Beach townhouse.
The $9.7 million Jupiter mansion he shared with Kimberly? Still co-owned by both of them, interestingly enough. It's a lingering tie to a relationship that lasted six years but ultimately couldn't go the distance.
Where is Kimberly Guilfoyle now?
If you're wondering how the ex-fiancée is taking all this, she’s busy. Very busy.
Kimberly Guilfoyle didn't exactly go away quietly—she went to Greece. In a move that many political observers called "strategic banishment," President Trump nominated her as the U.S. Ambassador to Greece. She was sworn in and moved to Athens in late 2025.
"I’m happy for Don," Guilfoyle told the New York Times in early January 2026. "I wish him, of course, all the best."
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Despite the public well-wishes, insiders claim she’s been skeptical of the new match. There’s a lot of history there, and moving on from a six-year engagement while your ex-fiancé proposes to a younger socialite within a year isn't exactly a walk in the park. But for now, she’s focusing on Greek-American relations and, according to her own jokes in interviews, looking for a "new husband" in Athens.
What This Means for the Trump Family Brand
This isn't just a gossip story; it’s a shift in the brand. Don Jr. is often seen as the "heir apparent" to the MAGA movement, the one who connects most with the base. Bringing in someone like Bettina Anderson—who is more "Old Palm Beach" than "Fox News Firebrand"—suggests a slight pivot toward a more polished, traditional image for the eldest son.
They look the part.
Whether this relationship leads to a massive televised wedding or a quiet ceremony at Mar-a-Lago remains to be seen. But for anyone still wondering who is Trump Jr dating, the search is over. It’s Bettina Anderson, and she’s already picked out the "chunky diamond ring" that’s been seen on her finger since late 2025.
If you are following the evolving social landscape of Palm Beach and the Trump inner circle, keep an eye on:
- The Paradise Fund Events: This is where Bettina is most active and where you'll likely see the couple making their most frequent "official" appearances.
- Property Records: Watch the Jupiter, Florida mansion. Once that property is sold or transferred, it’ll be the final legal sign that the Guilfoyle era is officially closed.
- White House Social Calendars: As the daughter-in-law-to-be, expect Anderson to be a mainstay at upcoming state dinners and holiday events throughout 2026.