Kimberly Guilfoyle joins ex Don Jr for DC inauguration events, faces awkward run-in with Bettina Anderson

WASHINGTON, DC: Donald Trump Jr was making his rounds in DC this weekend ahead of his father’s big inauguration - albeit with some unexpected company.

The eldest Trump son was spotted Saturday, January 18, alongside his ex-fiancee Kimberly Guilfoyle as they greeted Eduardo Bolsonaro — the son of former Brazilian President Jair Bolsonaro — and his wife, Heloísa Wol.

Furthermore, Don Jr’s new girlfriend Bettina Anderson and ex-fiancee Guilfoyle, found themselves in an awkwardly close encounter Sunday night as they both attended pre-inauguration events.

The reunion between Don Jr and Guilfoyle was surprisingly relaxed and comfortable, raising plenty of eyebrows as the two mingled with their Brazilian counterparts.

Eduardo captured the moment in a video on his Instagram Stories. “🇺🇸🤝🇧🇷 Time to celebrate buddy,” he captioned the post, tagging Don Jr. The latter reposted it to his own followers.

Don Jr’s relationship drama with Kimberly Guilfoyle

Don Jr reportedly called it quits with Guilfoyle last year and moved on with Palm Beach socialite Bettina Anderson. “Kimberly and I will never stop caring for each other and will always keep a special bond,” Don Jr assured Page Six just last month.

While the exes seemed pretty amicable this weekend, the same can’t be said for the Trump family’s feelings about Don Jr’s new girlfriend. Seven anonymous Trump family friends dished to Mediaite that they’re not exactly fans of Anderson.

“Individuals close to the president have expressed growing concerns about the potential liability posed by his son’s new relationship,” one insider told the outlet. Another friend apparently took it upon themselves to warn Don Jr directly. “I told him that she’s not someone he should be around, and let him know about her past,” they spilled.

According to these sources, Anderson has a rep for partying and dating wealthy men in Florida. Anderson’s team, however, has strongly denied these allegations.

Even President Donald Trump is reportedly unimpressed. A family insider claimed Trump “does not approve” of the relationship and sees Anderson’s presence as “a liability rather than an asset.”

Awkward encounter between Kimberly Guilfoyle and Bettina Anderson

Dressed to the nines in a gorgeous dark ballroom gown, Anderson attended the candlelight dinner for President-elect Trump at the National Building Museum. Earlier in the evening, Anderson had her official debut by appearing in a family photo during a fireworks display at Trump National Golf Club in Sterling, Virginia.

The photo op was part of the festivities leading up to Monday’s swearing-in ceremony. Meanwhile, Guilfoyle wasn’t about to let anyone steal the spotlight. She took to Instagram to post a photo of herself at the same candlelight dinner.

That said, Monday’s inauguration is set to be Anderson and Don Jr’s first major public event as a couple. Guilfoyle will also be in attendance.

"Anderson is supposed to be there, so there will be some tension if both she and Guilfoyle are in the room," Daily Mail Kelly Laco reportedly said.

Bolsonaro meet and greet

Meanwhile, Eduardo Bolsonaro was in DC for the inauguration, but his dad Jair Bolsonaro was noticeably absent. The elder Bolsonaro — nicknamed the “Trump of the Tropics” for his MAGA-esque politics — is stuck in Brazil after his passport was confiscated last November.

This was after he was accused of plotting an alleged coup following his loss in the 2022 election. Brazilian Supreme Court Justice Alexandre de Moraes, a known Bolsonaro adversary, denied his request to travel to the US for Trump’s swearing-in.

Eduardo wasn’t shy about calling foul, telling Folha de São Paulo on Friday that Moraes’s decision was nothing more than “interference” from Brazil’s new president Luiz Inácio Lula da Silva, who defeated his father.

Eduardo is hopeful that a second Trump administration could turn the tables. He’s even speculated that US authorities might revoke Moraes’s visa, citing the justice’s “brutally aggressive behavior” and last year’s temporary ban on Elon Musk’s X (formerly Twitter) for spreading misinformation in Brazil. The platform eventually paid a $5 million fine to resolve the issue.

“In my opinion, there is a real risk that Alexandre de Moraes will lose his visa to enter the United States,” Eduardo told the paper. “Especially if he shows signs of such brutally aggressive behavior, not only against Brazilians but also against American authorities.”

Republican lawmakers have already taken sides. Last year, a group of GOP heavyweights including Senator Rick Scott and several House representatives called on the State Department to ban Moraes, accusing him of “acting like a totalitarian dictator.”

As for Don Jr and Eduardo, the pair appeared rather chummy in the Instagram video. “Please give your dad my best,” Don Jr said as they shook hands for the camera. The rest of the audio was muted to conceal their conversation, per the Daily Beast.

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