Kimberly Guilfoyle’s Public Birthday Message to Don Jr. Sparks Debate Amid New Romance With Bettina Anderson

Donald Trump Jr.’s 47th birthday post drew more attention than expected—because of who showed up in his mentions.

Just as Don Jr. publicly debuted his relationship with new girlfriend Bettina Anderson at his father’s high-profile New Year’s Eve bash, his former fiancée, Kimberly Guilfoyle, posted a glowing birthday tribute to him on Instagram—complete with photos of the two during happier times.

What might have passed as a harmless social media gesture quickly triggered waves of speculation. Was it a show of grace—or something more complicated?

The message came just weeks after Don Jr. confirmed his split from Guilfoyle, following months of behind-the-scenes rumors and a string of public appearances with Anderson.

A Sweet Message With a Strange Timing

Kim Guilfoyle wished Donald Trump Jr. a happy birthday in a heartfelt Instagram story post

Don Jr. and Bettina Anderson were seen smiling on their way inside Donald Trump’s New Year’s Eve party

Guilfoyle’s post comes after the pair amicably broke off their engagement

On her Instagram story, Guilfoyle, 55, posted a collage of smiling memories, calling Don Jr. “one of the most passionate, determined men I’ve ever known.”

But the well-wishes arrived on the same day Don Jr. was photographed walking the red carpet with Anderson at Mar-a-Lago, flashing smiles and fielding questions about their relationship.

Anderson, a 38-year-old socialite and former model, has stirred up chatter among Trump supporters who question her conservative credentials. But none of that seemed to slow down the couple’s big public moment.

The juxtaposition between Guilfoyle’s post and Don Jr.’s new PDA with Anderson was too sharp to ignore.

A Public Goodbye—Or Something Else?

The birthday post reignited interest in what many insiders have called a “quietly messy” split.

Friends close to Guilfoyle told DailyMail.com she was “blindsided” by the now-infamous photos of Don Jr. and Anderson out to dinner in Palm Beach three months ago—images that surfaced before he had formally announced the breakup.

“Kimberly either didn’t know about Bettina—or didn’t want to know,” one friend said. “She’s no fool, but it’s easy to deceive yourself when you’re deeply committed to someone.”

Guilfoyle and Don Jr. got engaged in 2022, after four years together. The engagement ended quietly, with no public fallout—until now.

Meet Kimberly Guilfoyle, Trump’s new pick for ambassador to Greece

Anderson, a model and socialite, has caused a stir among some Trump supporters who claimed she is not ‘MAGA’ enough

Rumors about Don Jr. and Anderson’s relationship spawned when the couple started going out together months before Don Jr. addressed that he was no longer engaged

Bettina Anderson seen with Don Trump Jr and ex-wife at party

Don Jr. and Anderson, 38, rang in the New Year alongside other prominent members of Trump’s group, including ‘First Buddy’ Elon Musk and Vice President-elect JD Vance.

A Love Triangle Played Out in Public

While Don Jr. praised Guilfoyle’s new role as U.S. ambassador to Greece in a statement to Page Six, calling her “someone I will always care for,” the timing of the statement did little to cool online speculation.

“This looks like an emotional chess game—public affection vs. quiet tribute,” one commenter wrote on X. “And somehow it feels like neither side is done.”

Anderson’s arrival on the scene has been polarizing. Critics have labeled her a “Florida party girl” and “not MAGA enough.”

One photo of her wearing a mask next to a COVID-19 awareness sign circulated widely among right-wing accounts, with users accusing her of being a “social climber.”

A Verse, A Vibe, A Message?

In what many read as a subtle clapback, Anderson shared a Bible verse from Exodus on her social media shortly before the New Year:

“So let them lie. Let them manipulate. Let them talk. You just be still, because when God is on your side, who can stand against you?”

The quote raised eyebrows—and led some to believe she was aware of the whispers and criticism brewing around her relationship.

The Bigger Picture: A GOP Image Dilemma

This unusual triangle—Don Jr., his ex-ambassador fiancée, and his new socialite girlfriend—has sparked a wider debate in Republican circles.

“Optics matter. And this one’s messy,” one GOP strategist told the press.

Some Trump insiders have reportedly warned that Anderson’s image could be a distraction as Trump builds his post-election narrative and courts the MAGA base.

Others argue that Don Jr. has a right to his personal life, regardless of the political optics.

But the timing of Guilfoyle’s tribute—landing just as Don Jr. leaned into his new romance—has only added layers of complexity to what had been a quiet breakup.

“Posting that collage wasn’t an accident,” one source said. “It was a public reminder. She’s still part of the narrative—whether they like it or not.”

Final Word: More Than a Birthday Message

Don Jr. may have wanted his birthday to be about fresh starts, new love, and flashy appearances.

But Kimberly Guilfoyle’s unexpected post pulled the past into the present—and reignited a conversation that had never fully cooled.

As of now, neither Guilfoyle nor Anderson has made any direct comment about each other.

But fans and followers have made their opinions clear:

“You can break off an engagement,” one post read. “But it’s harder to break the internet.”