Although Donald Trump Jr. and right-wing media personality Kimberly Guilfoyle have not officially broken up their engagement, rumors are spreading after Trump Jr. was spotted in Palm Beach on Monday with another woman: model/influencer Bettina Anderson. The pair’s romance is reportedly an “open secret” in the area.

As Jimmy Kimmel explained in his monologue Tuesday, “The first boy has not made an announcement about the status of his relationship with former Fox Newser Kimberly Guilfoyle, but something sure seems to be up.”

He showed Donald Trump’s Truth Social post announcing that he was appointing Guilfoyle as the US ambassador to Greece, noting that the president-elected posted this “less than 24 hours” after the photos of Don Jr. and Anderson were published.

“He made her ambassador to one of the farthest countries possible,” said Kimmel.

“What a family this is,” Kimmel mused. “He has more relatives working at the White House than I do at this show right now.”

The Late Night host also bashed Trump for reportedly lobbying to have Florida Gov. Ron DeSantis appoint his daughter-in-law, Lara Trump, to Marco Rubio’s soon-to-be vacant Senate seat.

“Remember when Republicans couldn’t shut up about Kamala Harris and her qualifications? ‘She doesn’t have the experience. He only picked her because she’s a Black woman. Is she even a Black woman?‘” Kimmel recalled.

“Well, may I introduce Senator Lara Trump, ladies and gentlemen: graduated with a BA in communications at NC State, studied at the French Culinary Institute. Get that lady in government right away,” Kimmel joked.

Referring to Lara’s widely mocked music video in September, Kimmel said about the appointment, “Maybe it’s Trump’s way of telling her to please stop singing. I don’t know.”

The one bright side for Kimmel was that at least it doesn’t seem like the Florida Senate seat will go to former congressman Matt Gaetz.

“Starting in January, he will host a show on OAN, One America News,” Kimmel explained.

He added, ”For those who aren’t familiar with OAN, it’s like Fox News but crazier and younger, which is just the way Matt Gaetz likes it.”

Does Donald Trump Jr.’s Ex Kimberly Guilfoyle Have a New Boo?

Bettina Anderson, Donald Trump Jr.’s new girlfriend, posted a photo last week of what appeared to be a roughly $1,000 caviar set. It was unclear who purchased the gift, but it was seemingly meant to be enjoyed by Trump Jr.’s side.

“Ready for Valentine’s Day,” she wrote, alongside an emoji of two champagne glasses clinking.

Not one to be outdone, Kimberly Guilfoyle—Trump Jr.’s recent ex—posted a photo to her Instagram Stories this week showing an extravagant bouquet of pink roses she received from… well, it’s not entirely clear.

“Thank you,” the new U.S. Ambassador to Greece captioned the post, along with two pink heart emojis.

Per The Daily Mail, the roses were from Boutique Royal, a luxury flower shop in Miami, that retail for $250. A quick scroll through the shop’s website suggests that Guilfoyle’s bouquet was one of the shop’s more affordable offerings, as some of their floral arrangements cost almost $4,000.

The Mail also identified Anderson’s haul as the Grand Caviar Tasting Set from Portage Foods.

Donald Trump Jr. and Bettina Anderson attend Michael Rubin’s 2025 Fanatics Super Bowl Party at The Sugar Mill on February 08, 2025 in New Orleans, Louisiana. / Kevin Mazur/Getty Images for Fanatics
A Palm Beach socialite, Anderson was first spotted in the Trump entourage at the Republican National Convention in July, where she was pictured sitting behind Trump Jr. and Guilfoyle. A few months later, The Daily Mail published a doozy of a report claiming that the pair were spotted canoodling in Palm Beach. In one December outing, they were photographed holding hands.

Although Trump Jr. never officially confirmed his split with Guilfoyle, the first son told Page Six in a statement that the two would “never stop caring for each other” and would “always keep a special bond.”

“I could not be more proud of her and the important role she’ll continue to play in my father’s administration,” he continued referring to Guilfoyle’s ambassadorship to Greece.

He and Anderson then proceeded to hard-launch their relationship in January, attending several of his father’s inaugural festivities hand-in-hand.