Donald Trump Jr. Debuts New Girlfriend at Inauguration — All Under the Gaze of Ex-Fiancée Kimberly Guilfoyle

Despite alleged warnings from close friends of the Trump family, Donald Trump Jr. still chose to bring his new girlfriend, Bettina Anderson, to his father’s second inauguration.

And everyone noticed, including his ex-fiancée, Kimberly Guilfoyle.

All eyes were on every member, friend, and associate of the Trump family as expected during the Jan. 20 event. Aside from watching President Donald Trump himself, others were curious how Donald Jr. would handle having his ex-fiancée and his new model girlfriend in one room.

(L-R) Donald Trump Jr. brought his new girlfriend, Bettina Anderson, to his father’s inauguration with his ex-fiance, Kim Guilfoyle, watching nearby. (Photos by Mark Wilson/Getty Images) (Photo: @Bettina_Anderson/Instagram) (Photo: @kimguilfoyle/Instagram)

Luckily for him, all three people acted like “civil” adults about the matter, but according to People’s sources, Guilfoyle was definitely keeping an eye out.

The outlet reported one source who alleged, “Kim saw Don with Bettina and it was all civil. No negativity. She should be ambassador to Greece soon which is important to the administration, and she will be away a lot of the time. She is smart and dedicated. No need for animosity.”

According to the unnamed insider, despite there being no issues at the event, Guilfoyle nonetheless was still upset about the recent end of her relationship with Trump. Jr.

The two began dating in 2018 and two years later got engaged on New Year’s Eve. They parted ways in 2024, which was only confirmed after Trump Jr. was caught holding hands with Anderson in Florida on Dec. 9.

“Kim is still very fond of Don, and kept a watchful eye out. She knows how beautiful and well dressed Bettina is, and there is no question that she was hurt when her romance with Don ended,” the purported tipster said.

Guifoyle and Trump Jr. seem to have no ill feelings toward each other. In fact, they’ll have to see each other in the future since his father appointed the former Fox News host to be the U.S. ambassador to Greece.

Earlier this month, sources close to the family told Mediate that there were concerns about Trump Jr. dating Anderson due to her hard-partying past. The report claimed she was seen as a “liability” and that it would be best if he didn’t bring her to the inauguration. 

But according to new sources, Anderson, who is known as a socialite from a Florida banking family, knows how to handle herself. “She knows who she is, and is proud of her looks which she flaunts,” said the source. “But she understands that she needs to look and act responsible, and never overshadow the rest of the family.”

Many fans reacted to the report with mixed responses on People’s website

One person wrote in the comments, “I think he should have stayed with Kim.”

“I don’t think ANYONE is surprised,” said a second person, who continued, “Kimberly is NINE years older than him, he left his wife and FIVE children to hang with her and dragged out the ‘engagement’ (hope she keeps the ring) . She should have declined the invite and thank Donald in private for the appt. to Greece. Very HUMILIATING situation for Kimberly!”

Yet some believe Kim will be next to write about her time with the Trump family.

“Can’t wait for her tell-all in 4 years when the ambassadorship dries up,” wrote one person, while another said, “Bet if she wrote a tell all we’d get to hear all Don jr. DIRTY little secrets.”

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