It happened fast. One minute, they were the undisputed power couple of the MAGA movement, and the next, the internet was buzzing with news that Donald Trump Jr. and Kimberly Guilfoyle are reportedly splitting up. Honestly, if you’ve been paying attention to the Palm Beach social scene lately, the signs weren't exactly hidden. People have been whispering for months, but things really hit a boiling point recently when the "engagement that wouldn't end" finally seemed to hit a wall.
They were together for six years. That’s a lifetime in political years. But lately? The vibe shifted.
What Really Happened with the Power Couple?
The breakup wasn't a sudden explosion. It was more like a slow leak. Insiders have been telling outlets like Page Six and People that the pair had been bickering in public at Mar-a-Lago for a while. Not screaming matches, mind you, just that low-level "we're over this" bickering that anyone who’s been in a long-term relationship recognizes instantly.
Basically, the "holding pattern" of their four-year engagement became too much to ignore.
Then came the photos. Don Jr. was spotted in Palm Beach holding hands with socialite Bettina Anderson. It wasn't just a casual lunch; it was her 38th birthday, and they looked, well, very much like a couple. While the world was asking if Donald Trump Jr. and Kimberly Guilfoyle are reportedly splitting up, Don Jr. was seemingly already moving on.
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Interestingly, the Trump family doesn't seem to be "taking sides" in the way you might expect. Reports suggest the family is still "enamored" with Kimberly. She’s been a loyal soldier for years. But politics is a business, and sometimes the business requires a change of scenery.
The Greece "Promotion-Banishment"
Here is where it gets kinda wild. Right as the split rumors reached a fever pitch, Donald Trump Sr. announced Kimberly’s nomination as the U.S. Ambassador to Greece. Some call it a reward for years of loyalty. Others call it "shipping her 5,000 miles away" so Don Jr. can start his new chapter with Bettina without the awkwardness of running into his ex-fiancée at every Florida gala.
Kimberly is currently in Athens, living at the Jefferson House. She recently told the New York Times she’s "happy for Don" and wishes him the best. She even joked to Greek officials about looking for a "new husband." She’s a pro; she knows how to spin a narrative.
Why the Split Matters for the Trump Brand
You can't talk about Don Jr. without talking about the brand. For years, Kimberly was the firebrand at the podium, the one shouting "The best is yet to come!" at the RNC. She wasn't just a girlfriend; she was a key surrogate.
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When Donald Trump Jr. and Kimberly Guilfoyle are reportedly splitting up, it changes the optics of the inner circle. Bettina Anderson is a different vibe. She’s a Palm Beach socialite, a former model, and someone who fits into that "Waspy" circle that the former president reportedly finds impressive.
There’s also the matter of the $9.7 million mansion in Jupiter, Florida. They bought it together in 2021. Property records show they both still own it, even though Don Jr. has reportedly moved into Bettina’s townhouse. Untangling a six-year life is never as easy as a press release makes it sound.
The New Engagement
On December 15, 2025, during a White House Christmas reception, the news became official. Donald Trump Sr. himself announced Don Jr.'s engagement to Bettina Anderson.
- Don Jr. took the podium and said he was "at a loss for words."
- Bettina called him the "love of her life."
- The room was reportedly a bit stunned by the speed of it all.
It was a definitive end to the Kimberly era. While the public was still processing the idea that Donald Trump Jr. and Kimberly Guilfoyle are reportedly splitting up, the family had already moved the chess pieces.
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Navigating the Public Fallout
If you're following this saga, the best way to keep up is to watch the social media footprints. Kimberly has transitioned her content to her ambassadorial duties in Greece, focusing on international relations and, predictably, a lot of high-fashion diplomat looks. Don Jr., meanwhile, is leaning into the Florida socialite life.
If you're curious about the logistics of their split, keep an eye on the Jupiter property listings. That mansion is the last major tie they have. Once that sells, the "special bond" they claim to have will be strictly long-distance.
The lesson here? In the world of high-stakes politics and celebrity, even a six-year engagement and a massive diamond aren't a guarantee of a "happily ever after." Sometimes, a move to Athens is the only way to find a fresh start.