If you’ve been following the whirlwind of the second Trump administration, you’ve probably noticed a big change in the family photos. Gone is the high-decibel energy of Kimberly Guilfoyle. In her place? A poised, blonde Palm Beach socialite named Bettina Anderson.
It wasn't a subtle shift.
Honestly, the transition from the long-term Guilfoyle era to Donald Trump Jr girlfriend now—fiancée, actually—felt like a calculated rebrand. One minute Kim was shouting "The best is yet to come!" from a podium, and the next, she was being sworn in as the U.S. Ambassador to Greece, roughly 5,000 miles away from Mar-a-Lago.
The Engagement Everyone Saw Coming (Sorta)
Speculation had been bubbling for months, but the official word didn't drop until December 15, 2025. It happened during a White House Christmas party, of all places. President Donald Trump himself took the mic to announce that his eldest son had popped the question.
Don Jr. later confirmed the news to the room, saying, “She said yes, so that’s a big win for the end of the year.” Bettina, looking every bit the Florida chic archetype, thanked the President and Melania for their hospitality. It was a formal coronation of sorts.
For those keeping score, the timeline is a bit... messy.
Don Jr. and Bettina were first spotted looking cozy in Palm Beach back in late 2024. This was before the public even knew he and Kimberly Guilfoyle had officially called it quits on their four-year engagement. Insiders later claimed the split happened “amicably” before the 2024 election, but the optics were definitely a bit tangled.
Who is Bettina Anderson Anyway?
Bettina isn't some random newcomer to the high-society scene. She’s Palm Beach royalty, through and through.
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Her father was the late Harry Loy Anderson Jr., who made history by becoming the youngest bank president in the U.S. at just 26 years old. That kind of legacy carries weight in Florida.
- Age: 39 (as of late 2025)
- Background: Third-generation Palm Beach resident.
- Career: Primarily known as a socialite and model, she’s been involved with The Paradise Fund, a non-profit focused on disaster relief.
- Vibe: Much more "quiet luxury" than her predecessor.
There’s been a lot of chatter about why this match works for the Trump family. Sources close to the inner circle mentioned to The Daily Beast that Don Jr. was looking for someone who could "relax" a bit more. Apparently, the constant high-glam, professional dress code of the Guilfoyle years was starting to grate.
Bettina is often seen in more casual, albeit expensive, attire—think crisp white button-downs and linen rather than the structured, bold-colored sheath dresses that became Kimberly's trademark.
The Kimberly Guilfoyle "Exile" to Athens
You can’t talk about Donald Trump Jr girlfriend now without mentioning the elephant in the room: Kim.
The breakup wasn't just a romantic end; it was a professional pivot. In a move that many political observers called "promotion-banishment," President Trump nominated Guilfoyle as the U.S. Ambassador to Greece.
She was sworn in on September 29, 2025.
She seems to be leaning into it, though. In a January 2026 interview with The New York Times, she finally broke her silence on Don Jr.'s new engagement. Her response? "I'm happy for Don. I wish him, of course, all the best."
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Brief. Professional. Maybe a little cold?
Reports from People suggest she’s still "processing" how fast it all moved. Some sources claim she isn't entirely convinced the new relationship is built to last, suggesting Bettina might be more enamored with the Trump prestige than the man himself. But for now, Kim is busy in Athens, reportedly telling local officials she’s on the lookout for a “new husband.”
Living the Palm Beach Life
Don Jr. hasn't just changed partners; he’s changed his living situation.
For years, he and Guilfoyle shared a massive $9.7 million mansion in Jupiter, Florida. As of early 2026, property records show both names are still on the deed, but Don Jr. is rarely there.
He’s basically moved into Bettina’s townhouse in Palm Beach.
Locals say his car is a permanent fixture in her driveway. They’ve become a staple of the local gala circuit, appearing at everything from the amfAR Gala in Cannes to the FIFA Club World Cup final at MetLife Stadium.
Why the Family Prefers the New Dynamic
It’s no secret that the Trump family dynamic is... intense.
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According to insiders, the elder Trump "approves" of Bettina. The word is that he prefers her more understated (for Palm Beach) look and the fact that she doesn't try to "grandstand" or pull focus from the political mission.
Kimberly was a powerhouse fundraiser, but she was also a massive personality. In a family where there’s only room for one main star, Bettina’s more supportive, background role seems to fit the current administration's needs better.
What Most People Get Wrong About the Transition
People love a scandal, and the overlap between Kim and Bettina certainly provided one. But if you look at the evidence, this was a strategic realignment.
Don Jr. is 48 now. He’s got five kids with his ex-wife, Vanessa (who, in a wild twist of fate, is now dating Tiger Woods). He’s settled into his role as a political firebrand and crypto enthusiast.
Bettina represents a return to his Florida roots. She’s someone who knows the Palm Beach "code" and doesn't need to be taught how to navigate a high-society fundraiser.
What to Watch For Next
If you're keeping tabs on this relationship, there are a few things that will tell us if it’s truly "built to last," as the skeptics doubt.
- The Jupiter Mansion Sale: Keep an eye on the real estate listings. Once that $9.7 million home hits the market or one party buys the other out, the "untangling" from the Guilfoyle era will be complete.
- Campaign Trail Presence: With the 2026 midterms approaching, will Bettina take a mic? If she stays off the stage, it confirms the "supportive partner" rebrand.
- Wedding Planning: No date has been set for the Don Jr. and Bettina nuptials, but a White House wedding isn't off the table given the current administration.
The shift from Kimberly Guilfoyle to Bettina Anderson marks a new chapter for the Trump heir. It’s a move from the loud, aggressive energy of the "MAGA Queen" to a more traditional, old-money Florida vibe. Whether it's a "win for the end of the year" or a long-term match remains to be seen, but for now, Bettina is firmly entrenched as the leading lady in Don Jr.'s world.
To stay updated on this evolving story, you should keep an eye on Palm Beach property transfers and official White House guest lists for 2026. These public records often reveal more about the inner circle's stability than any anonymous source ever could.