Kimberly Guilfoyle’s “Revenge Dress” Returns—And Her Quiet Power Move This Spring Has Left Don Jr. Facing Questions He Thought Were Behind Him

It’s been nearly three months since Kimberly Guilfoyle’s now-viral Valentine’s Day Instagram post—where she wore a curve-hugging white dress, held a luxury bouquet of roses, and said only, “Thank you 💕💕.”

At the time, it was widely interpreted as a statement of independence, strength, and—perhaps—a final page turned after her split from Donald Trump Jr.

But now, in May 2025, with Guilfoyle preparing for her diplomatic assignment in Athens, Don Jr. ramping up campaign appearances with Bettina Anderson, and whispers of media deals circling both camps, one thing has become clear:

The breakup may be official. But the narrative? It’s still unfolding.

From Super Bowl Standoff to Spring Reset

Back in February, both Kimberly and Don Jr. attended the Super Bowl in Las Vegas. Don Jr. brought Bettina and several of his children. Kimberly attended separately—but within viewing distance, sparking tabloid speculation of a run-in.

The couple made no secret of their romance as Don Jr. took Anderson to the Super Bowl with his children – risking an awkward run in with Guilfoyle as she was also in attendance – and was seen taking pictures with celebrities including Kevin Costner.

The new couple took their relationship to the next level at the weekend, enjoying the Super Bowl together in a box with some of Don Jr’s children

Anderson cozied up to her new man and posed for photos with three of his five kids. His eldest daughter, Kai, did not appear to be in attendance

The couple also attended the Fanatics Super Bowl Party at The Sugar Mill one day prior, where they posed on the red carpet together

Anderson issued a subtle nod to President Trump at the Superbowl with her bathroom selfie

The couple risked an awkward run in with Guilfoyle as she was also in attendance, and was seen taking pictures with celebrities including Kevin Costner

It never happened.

But insiders now say the avoidance wasn’t coincidental—it was strategic.

“Neither of them wanted a confrontation,” one former aide said. “But neither was ready to pretend it was all water under the bridge either.”

Since then, Kimberly has leaned into her ambassador role, preparing for her formal relocation to Greece this summer while carefully curating an image of poised distance.

Meanwhile, Bettina has become a more visible fixture beside Don Jr.—including at multiple campaign fundraisers, where her presence has sparked mixed reactions.

Mothers’ Day Silence, Father’s Day Storms?

This past weekend, for Mother’s Day, Kimberly posted a throwback photo of her and her son with a caption: “Grateful for every minute. 💙”

It received tens of thousands of likes—and a notably warm repost from Ivanka Trump.

Bettina, on the other hand, posted from Mar-a-Lago, tagging several members of the Trump inner circle but—curiously—not Don Jr.

“It’s not always what they post,” one social media analyst said. “It’s what they don’t.”

Don Jr. himself has remained publicly neutral, though sources say he is “deeply aware” of the shifting dynamics around him—and that he’s become “increasingly cautious” about how both women’s stories are playing out in the media.

A Campaign Year Complication

Now that Trump has returned to the White House, Don Jr. is once again a central figure in the family machine—helping shape policy strategy, liaise with donors, and serve as a vocal face for the administration.

And that spotlight has intensified scrutiny over his personal life.

“Kimberly was always part of the MAGA inner circle,” one former strategist said. “She knew the language. The base trusted her.”

“Bettina is beautiful, smart—but her past posts, her parties, her old alliances… they’re giving people pause.”

That tension has grown louder after a recent resurfaced clip from 2020, in which Bettina voiced support for vaccine mandates—a position at odds with the Trump base.

Kimberly’s Quiet Countermove in Europe

As May unfolds, Guilfoyle has been spotted attending closed-door briefings at the State Department, alongside prep sessions with national security officials.

According to insiders, she is expected to begin her posting in Athens by late June, where she will focus on U.S.-Greece trade relations and regional defense strategy.

She has not commented on Don Jr. since February. Nor has she addressed Bettina directly.

But her recent public schedule tells a story of its own:

A panel at the Hudson Institute on women in diplomacy.
A working lunch with the Greek Foreign Minister.
A joint interview with CNN’s International Desk on “rebuilding trust between America and its allies.”

“She’s moving forward,” said one former Fox colleague. “But she hasn’t forgotten how to shape a headline without ever saying a word.”

Don Jr. Now Navigates Two Shadows

As Don Jr. doubles down on campaigning in Arizona, Michigan, and Wisconsin, he is increasingly asked about both Kimberly and Bettina—even if only off-record.

According to one GOP fundraiser, “there’s pressure to keep Bettina in the frame—but not too close.”

The tension is subtle. But it’s real.

“Kimberly brought political fluency,” the source said. “Bettina brings style and fresh optics—but she doesn’t know the terrain.”

And with the party base divided between loyalists who still admire Kimberly and newcomers embracing the shift, Don Jr. is now forced to walk a tightrope.

What Happens Now

With summer approaching, and Guilfoyle’s departure for Athens imminent, both she and Don Jr. appear to be embracing divergent paths.

But the echoes of February still linger.

The “revenge dress” moment, far from being a one-off, has become a symbol—of feminine autonomy, quiet power, and the ability to reclaim space in the public eye without needing permission or apology.

“She didn’t get petty. She got diplomatic,” said a Washington insider. “That’s the real power move.”

And Don Jr.? He may have moved on. But he hasn’t moved far enough to escape comparison.

Conclusion: Some Messages Don’t Need Words

Kimberly Guilfoyle didn’t write a memoir. She didn’t tweet a takedown.
She posted a dress. A bouquet. A two-word caption.

And now, in May 2025, the story still lingers—not as gossip, but as a case study in how image, timing, and silence can say more than speeches.

She’s boarding a flight for Europe.
He’s criss-crossing battleground states with a new hand in his.

But the moment remains—white dress, pink roses, “thank you.”
And for everyone watching, the real question still stands:

Who really had the last word?