It was the engagement that seemed like it would never actually end in a wedding. For six years, Donald Trump Jr. and Kimberly Guilfoyle were the undisputed power couple of the MAGA universe. They were everywhere—on the campaign trail, at Mar-a-Lago, and in those viral, high-energy videos that defined a specific era of political theater. But then, the silence got louder.
People started noticing things. The joint appearances dried up. The Instagram tags stopped. Honestly, by the time the official news broke, most of the "inner circle" had already moved on.
So, what happened to Don Jr and Kimberly Guilfoyle exactly?
The Quiet Split and the Palm Beach Hand-Holding
The relationship didn't end with a dramatic press release. It ended with a photograph. In December 2024, Don Jr. was spotted in Palm Beach holding hands with Bettina Anderson, a well-known Florida socialite.
The internet went into a frenzy.
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At that moment, the world realized the engagement to Kimberly—which had been official since New Year's Eve 2020—was effectively over. Sources later told People and Page Six that the couple had been bickering in public for months. They weren't getting along. They were "argumentative" at Mar-a-Lago. It wasn't some sudden explosion; it was a slow burn that finally ran out of fuel.
Where Kimberly Guilfoyle Is Now
You might think a breakup with the former president's son would mean a quiet exit from the stage. Not for Kimberly. In a move that some insiders called a "promotion-banishment," Donald Trump nominated Guilfoyle to be the U.S. Ambassador to Greece shortly after the split became public.
She's currently living in Athens.
In January 2026, Kimberly broke her silence in a profile with The New York Times. She didn't dish the dirt. She kept it professional, mostly. "I’m happy for Don," she said. "I wish him, of course, all the best." It was a classic diplomatic pivot, though friends of hers have suggested she’s still processing how quickly things moved on the other side.
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While she's busy overseeing drilling rights in the Ionian Sea and attending high-society events in Greece, her life in Florida is still technically "tangled."
- The Mansion: They still jointly own a $9.7 million estate in Jupiter, Florida.
- The Move: Reports from early 2026 indicate Don Jr. has "essentially" moved into Bettina Anderson’s townhouse.
- The Belongings: Even as recently as late 2025, Don’s clothes and shoes were reportedly still at Kimberly’s place.
Breakups are messy. Even when you're an ambassador.
Don Jr’s New Chapter with Bettina Anderson
While Kimberly was packing for Athens, Don Jr. was moving fast. At a White House Christmas reception in December 2025, President Trump himself took the podium to share some "happy news."
Don Jr. is engaged to Bettina Anderson.
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The timing was... interesting. They had been dating for about a year, meaning the transition from Kimberly to Bettina happened almost instantly. According to sources close to the family, the President "approves" of the new match. There’s a feeling among some in the Trump orbit that Kimberly had become a bit of a "grandstander," while Bettina fits a more traditional Palm Beach social mold.
Why the Split Still Matters in 2026
This isn't just tabloid fodder. This was a merger of two of the most influential voices in Republican politics. For years, Kimberly was the one who could fire up a crowd before the main event. Her absence from Don Jr.'s immediate side changes the dynamic of his future political aspirations.
He's now focused on his own media ventures and his role within the 2026 political landscape. Meanwhile, she’s building a legacy in international diplomacy.
They spent six years together. They share a massive real estate portfolio. They have a combined six children from previous marriages who grew up together. You don't just walk away from that without a lot of legal and emotional paperwork.
Actionable Insights for Following the Story
If you're trying to keep up with the fallout, here is what to keep an eye on over the next few months:
- Watch the Jupiter Property Records: The sale of their $9.7 million mansion will be the final signal that the financial "divorce" is complete.
- Monitor Embassy Dispatches: Kimberly's performance in Greece is being closely watched by both her supporters and critics of the "MAGA-to-Diplomat" pipeline.
- Look for Wedding Dates: Don Jr. and Bettina Anderson haven't set a date yet, but a 2026 wedding in Palm Beach is the heavy rumor.
Basically, they've both moved on, but the shadow of their six-year partnership is still very much present in the way they're navigating their new lives.