If you were scrolling through social media at the start of 2026 and wondered why the firebrand duo of Don Jr and Kimberly Guilfoyle seemed to have vanished from the same frame, you aren't alone. For years, they were the high-decibel heartbeat of the MAGA movement. They traveled the country together, spoke back-to-back at rallies, and eventually got engaged on New Year’s Eve in 2020. But things look a lot different now.
They’re done.
It wasn’t a sudden, explosive exit—at least not publicly. Instead, the relationship that many thought would lead to a massive Mar-a-Lago wedding quietly dissolved in late 2024. By the time 2025 rolled around, the shift was official, even if the press releases were sparse. Don Jr. has moved on to a new chapter with socialite Bettina Anderson, while Kimberly Guilfoyle has quite literally moved across the world.
The Breakup Nobody Saw Coming (But Everyone Suspected)
Rumors are a constant in the Trump orbit, but the silence between Don Jr and Kimberly Guilfoyle became deafening by mid-2024. People noticed they weren't posting the same hunting trips or political stops anymore.
Then came the White House announcement in December 2025. President Trump himself revealed that Don Jr. was engaged to Bettina Anderson. It was a classic Trump move: bold, public, and a little bit awkward for the ex. While some tabloids suggested the split was "not contentious," insiders told People that the emotional untangling took months. Apparently, Don Jr. still had clothes and shoes at Kimberly’s place well into 2025.
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Honestly, it's kinda wild how fast the "traditional" relationship she often spoke about was swapped for a new Florida life.
Why did they split?
Sources close to the family hinted that the dynamic changed once the campaign energy shifted. There was talk about Kimberly becoming a "grandstander," or perhaps trying to pull too much of the MAGA spotlight onto herself. In the Trump family, there’s usually only room for one sun to orbit.
Where is Kimberly Guilfoyle Now?
If you're looking for Kimberly, don't check Florida. She’s currently serving as the U.S. Ambassador to Greece.
Talk about a pivot.
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Nominated by Donald Trump in late 2024 and confirmed by the Senate in September 2025, she’s become what the New York Times recently called "the talk of Athens." It’s a massive role for the former Fox News host. She’s already making waves by being just as blunt as she was on the campaign trail, recently clashing with the Chinese embassy over their influence in Greek ports.
- Her current status: Thriving in a diplomatic role.
- Social life: She’s reportedly enjoying a "bustling" social scene in Athens.
- Relationship status: Single, though she jokingly told diplomats she might "work on getting a new husband" while in Greece.
Don Jr’s New Chapter with Bettina Anderson
While Kimberly is navigating the Mediterranean, Don Jr. is doubling down on his life in Palm Beach. His engagement to Bettina Anderson marks a significant shift in vibe. Anderson is a socialite who fits right into the high-society Florida world that the Trumps inhabit.
The couple was first spotted together holding hands a year before the engagement was official. Since then, they've been everywhere from the World Cup to inaugural parties. President Trump seems to approve, too. He famously remarked that he’s happy with the way Bettina looks and wants his son to be "satisfied" this time around.
Basically, the era of the "Guilfoyle-Trump" political powerhouse is over, replaced by a more localized, Florida-centric partnership.
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The Timeline of a Falling Out
- 2018: Don Jr. and Kimberly start dating after his split from Vanessa Trump.
- 2020: They get engaged on New Year's Eve (though they didn't announce it for a while).
- 2024: The relationship quietly ends. Don Jr. begins dating Bettina Anderson.
- Late 2024: Trump nominates Kimberly for the ambassadorship in Greece.
- September 2025: Senate confirms Guilfoyle's new role.
- December 2025: Official engagement of Don Jr. and Bettina Anderson announced at the White House.
It’s been a whirlwind. Kimberly recently broke her silence in a January 2026 interview, saying simply, "I'm happy for Don. I wish him, of course, all the best." It was diplomatic—fitting for her new job—but sources say she still has doubts about whether the new relationship is built to last.
Actionable Insights for Following the Story
If you want to keep tabs on how this drama or the political careers of Don Jr and Kimberly Guilfoyle evolve, here is what to do:
- Monitor Official State Department Cables: Since Kimberly is now a diplomat, her influence is more about policy than stump speeches. Look at her work regarding Piraeus and Chinese investment.
- Watch the 2026 Social Scene: Don Jr. and Bettina Anderson are staples of the Palm Beach circuit. Their wedding is expected to be one of the biggest social events of the year.
- Check Kai Trump’s Socials: Don Jr.’s daughter, Kai, has become a significant figure in her own right. Her interactions (or lack thereof) with Bettina often reveal more about the family dynamic than any official statement.
The landscape of the Trump family has changed. The "fire and brimstone" duo is now a memory, replaced by a diplomat in Athens and a newly engaged power player in Florida.