Rumors move fast in Palm Beach, but the fallout from the split between Donald Trump Jr. and Kimberly Guilfoyle moved even faster. Basically, by the time most people realized the "MAGA power couple" was on the rocks, Don Jr. was already being spotted around Florida with a new face. That face belongs to Bettina Anderson, a socialite who has lived in the Palm Beach scene for generations.
Honestly, the timeline is a bit of a mess. For years, Don Jr. and Kimberly were the face of the Trump campaign trail, always together, always loud, and seemingly solid after their 2020 engagement. But things changed. Reports started surfacing that they were bickering in public at Mar-a-Lago. Not just a little "where should we eat?" spat—insiders described it as argumentative. While the public still thought they were planning a wedding, the reality was that they were essentially living separate lives.
The Public "Soft Launch" of Bettina Anderson
It wasn't a press release that broke the news. It was a series of photos. Back in late 2024, Don Jr. was seen holding hands with Bettina Anderson in Palm Beach. People were stunned. At that point, he was still technically engaged to Kimberly.
You've probably heard the term "soft launch" on social media. This was more like a hard pivot. While Kimberly was busy being nominated as the U.S. Ambassador to Greece, Don Jr. was being seen at bars and dinners with Bettina.
Bettina isn't a newcomer to high society. She’s the daughter of the late Harry Loy Anderson Jr., a big-deal banker. She’s polished, she’s "Palm Beach royalty," and she carries a vibe that is vastly different from Kimberly’s high-energy, televised persona. Sources told Page Six and People that Don Jr. felt Bettina would impress his father more. Apparently, he had been griping that Kimberly was "too uptight" and dressed too professionally all the time. He wanted someone who looked "relaxed."
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Did He Actually Dump Kimberly for Bettina?
The word "dumped" is heavy, but the timing makes it look like a classic transition. Insiders claim Don Jr. and Bettina had been seeing each other for about six months before the split from Kimberly was official. If you do the math, that means there was a significant overlap.
Here is how the transition actually looked:
- The Overlap: While still engaged to Kimberly, Don Jr. reportedly took Bettina on a trip to Alaska. He was introducing her as his girlfriend to close friends while the rest of the world still saw him with Kimberly.
- The "Ambassador Escape": Just as the rumors reached a fever pitch, Donald Trump Sr. announced Kimberly’s nomination for the ambassadorship in Greece. Talk about a "soft landing." It was a way to move her 5,000 miles away without it looking like a messy family feud.
- The White House Announcement: Fast forward to December 2025. At a White House holiday party, the President himself announced that Don Jr. and Bettina were engaged. Kimberly was already in Athens by then.
Kimberly Guilfoyle’s Reality in Athens
You’d think she’d be bitter, right? Well, she’s a pro. In a recent interview with The New York Times, she kept it classy—mostly. She said, "I'm happy for Don," and wished him the best. But sources close to her say she was hurt. She had spent years building the MAGA brand alongside him.
Interestingly, despite the engagement to Bettina, Don Jr. and Kimberly still technically own a $9.7 million mansion in Jupiter, Florida together. They haven't sold it yet. Even though he’s "essentially living" in Bettina’s townhouse and Kimberly is in the official ambassadorial residence (Jefferson House) in Athens, they are still financially tied.
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Who Exactly is Bettina Anderson?
If you aren't from Florida, you might not know her. Bettina is 39, a third-generation Palm Beach resident, and a Columbia grad with a degree in Art History. She’s a model and a philanthropist who co-founded The Paradise Fund.
Basically, she represents the "old money" aesthetic that the Trumps have always circled. Some sources say she’s a better fit for the family's current vibe. Even President Trump reportedly gave his blessing, with insiders saying he likes "the way she looks" and wants his son to be happy.
The Current Dynamic
Right now, it’s all "civil." There was no public drama during the 2025 inauguration events, even though both women were present. Kimberly kept a "watchful eye," but there were no scenes.
Is it built to last? Kimberly reportedly doesn't think so. She’s told friends she thinks Bettina is more interested in the "prestige" of the Trump name. But for now, Don Jr. seems all in. He’s traveling the world with Bettina—from Serbia to the FIFA Club World Cup—and they look very much like a couple ready for the altar.
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What to Watch For Next
If you're following this story, the next big steps aren't just about wedding bells. Watch for these three things:
- The Jupiter Mansion Sale: Once that $9.7 million house hits the market, the final tie between Don and Kimberly is officially cut.
- The Wedding Venue: Rumors are swirling about a White House wedding. If that happens, it’s a massive signal of Bettina’s total integration into the inner circle.
- Kimberly’s "New Husband" Quest: She’s already joked to Greek officials that she’s looking for a new husband in Athens. A high-profile European romance for her would be the ultimate "revenge" move.
The transition from Kimberly to Bettina wasn't just a breakup; it was a rebranding of Don Jr.'s public life. Whether it’s a "natural fit" or a temporary spark, the landscape of the Trump inner circle has officially shifted.
Practical Next Steps: If you want to keep up with the shifting dynamics of the Trump inner circle, keep an eye on official property records in Palm Beach County for the Jupiter mansion sale, and follow the social media accounts of The Paradise Fund to see Bettina’s public appearances. These are usually the first places where the next phase of their relationship will be visible before it hits the tabloids.