In a moment that felt both unexpected and inevitable, Donald Trump Jr. has confirmed the end of his long-standing relationship with Kimberly Guilfoyle—while simultaneously making headlines with a very public dinner date alongside a new romantic interest: Bettina Anderson.

The reveal wasn’t made through tabloid leaks or cryptic Instagram posts—it came straight from Don Jr. himself, in an exclusive statement to Page Six that blended diplomacy, affection, and unmistakable finality.

“Kimberly and I will always care for each other and maintain a unique bond,” Trump Jr., 46, shared.
“I couldn’t be prouder of her and the role she will continue to play in my father’s administration.”

Guilfoyle’s Next Chapter: An Ambassador’s Seat—and a Shadow of Controversy

The statement was timed closely with news that Kimberly Guilfoyle is set to be nominated as U.S. Ambassador to Greece under a potential second Trump administration—a move that stunned even seasoned Washington insiders.

While the nomination has been met with both praise and skepticism, Trump Jr. was quick to defend his former fiancée against renewed scrutiny tied to her controversial 2018 departure from Fox News, which reportedly involved an unresolved harassment allegation—an allegation Guilfoyle has long denied.

“Anyone resorting to unfounded and trivial tabloid attacks against her is only embarrassing themselves,” Trump Jr. said.

Still, the nomination process may prove rocky. Senate aides have already hinted at “serious vetting,” and multiple sources expect Guilfoyle’s personal history with the president’s son to resurface during confirmation hearings.

The Palm Beach Reveal: Trump Jr. and Bettina Go Public

Just 48 hours after the ambassador announcement, Trump Jr. appeared hand-in-hand with socialite and former model Bettina Anderson at the upscale Palm Beach hotspot Buccan—just a few miles from her West Palm Beach townhouse. Dressed in a sharp navy suit and open-collared white shirt, Don Jr. made no effort to hide their chemistry.

Anderson, clad in elegant black slacks and a sleeveless top, matched his confidence. Their fingers remained intertwined as they exited the restaurant and climbed into his truck.

According to sources close to the Trump inner circle, the couple has been seeing each other quietly for months—but Don Jr. had been hesitant to go public until now.

“He’s captivated by Bettina—her elegance, intelligence, and presence,” one insider said.
“Now that Kim is officially out of the picture, he’s ready to let the world know.”

Insiders Speak: Why Kimberly & Don Jr. Drifted Apart

While neither party has confirmed the precise reasons for the breakup, sources say the cracks began to show in March 2025, during Guilfoyle’s 55th birthday party. The celebration, held at their home in Jupiter, Florida, drew hundreds of guests—but Trump Jr. reportedly disappeared midway through the evening, retreating to his private suite.

Some insiders say Don Jr. had grown weary of Guilfoyle’s increasingly flamboyant public persona, her revealing wardrobe, and a party-centric lifestyle that clashed with the more disciplined tone now favored by the Trump political brand.

“She’s still the life of the party,” one Fox colleague commented. “But the Trump campaign isn’t looking for party energy right now. They’re looking for polish.”

A New Fit for a New Era?

In contrast, Anderson’s background seems to align more closely with the Trump family’s evolving image. She’s been photographed at high-end charity events, has long moved in elite Palm Beach circles, and—according to one source—“fits the brand.”

“Don Jr. has always wanted to impress his father,” a longtime family acquaintance told People.
“And someone like Bettina—classy, well-connected, media-trained—is a great way to do that.”

Her presence at Mar-a-Lago this week, seated beside Don Jr. at a high-profile dinner, confirms that their relationship has officially entered the public phase. Observers noted that the two “didn’t try to hide it at all”—laughing, whispering, and exchanging glances during the buffet line.

A Shift in Tone and Sobriety

Another subtle but telling factor in Don Jr.’s recent pivot? Sobriety.

While Guilfoyle is not known for excessive drinking, her fondness for cocktails is well-documented—earning her the nickname “Margarita Girl” during her early Fox News years. By contrast, the Trump family, led by the teetotaling Donald Sr., has long viewed alcohol with wariness, especially after the tragic loss of Fred Trump Jr. to alcoholism.

“Don takes his sobriety seriously,” a family friend confirmed. “That lifestyle matters to him—and to his father.”

Anderson reportedly shares similar values, adding another layer of compatibility to the budding relationship.

What’s Next: Ambassadorship, Election Year, and a New Power Couple?

As Kimberly Guilfoyle prepares for what could be the most high-stakes role of her career, her former partner is forging a new personal chapter—one that may quickly become a political asset.

Whether Anderson will play a public role in the Trump 2024 campaign remains unclear, but those close to the family see her as “a steady presence”—someone who won’t overshadow the candidate or the brand.

“Don’s been through a lot—public scrutiny, political pressure, personal transitions,” one insider said.
“Bettina brings calm. She’s not trying to be a celebrity. She’s just the right match for where he is now.”

Final Thought: The End of One Era, the Quiet Beginning of Another

In politics, few breakups end quietly. Fewer still come with grace.

Yet somehow, Donald Trump Jr. and Kimberly Guilfoyle have managed to part ways without scandal—or headlines filled with bitterness. And that, in this moment of personal and political transition, may be the biggest surprise of all.

Because while Guilfoyle heads toward an ambassadorship, and Don Jr. steps forward with Bettina on his arm, both seem focused on what’s next.

And neither is looking back.