Donald Trump Jr found himself in a whirlwind of personal and political dynamics during his father’s second inauguration on January 20. The president’s eldest son was spotted with his new girlfriend, Palm Beach socialite Bettina Anderson. Meanwhile, his former fiancée, Kimberly Guilfoyle, was also in attendance.
There were possibilities of tension; however, insiders reveal that there was no drama between Don Jr., Bettina, and Guilfoyle during the inauguration events. “Kim saw Don with Bettina, and it was all civil. No negativity,” a source close to their circle shared with PEOPLE.
However, Guilfoyle, who was recently nominated as the U.S. ambassador to Greece by Donald Trump, seemed to keep a close watch on her ex-fiancé throughout the weekend. “Kim is still very fond of Don, and kept a watchful eye out,” the insider noted. “She knows how beautiful and well-dressed Bettina is, and there’s no question that she was hurt when her romance with Don ended.”
Guilfoyle and Donald Trump Jr. were once a power couple in MAGA circles. They started dating in 2018 and were engaged on New Year’s Eve in 2020. However, by December 2024, the pair had quietly shut the doors on their engagement. Just weeks after Donald Trump’s election victory, Don Jr. was spotted holding hands with Bettina Anderson which signaled a start of a new chapter in his love life.
The timing raised eyebrows because Guilfoyle’s nomination as ambassador to Greece coincided with the public reveal of Don Jr.’s relationship with Anderson. “Kim has always been loyal to the Trump family, and she and Don Jr. remain friends,” an insider confirmed.
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Bettina Anderson, known for her confidence and social flair, quickly made an impression in Trump’s Palm Beach circles. A source described her as “social, sassy, and confident,” adding that she knows how exactly to handle the spotlight.
Meanwhile, whispers about Anderson’s motives have surfaced in social circles as some have started questioning whether her relationship with Don Jr. is more about boosting her visibility within the Trump orbit. Some insiders have also claimed that she lacks the political drive that Guilfoyle has displayed throughout her career.
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“Bettina understands that she needs to look and act responsibly and never overshadow the Trump family,” a source explained.
Anderson, no doubt, draws a lot of praise for her charm and poise. On the other hand, Guilfoyle’s work ethic and political expertise continue to set her apart. “Kim is smart, dedicated, and deeply committed to the MAGA movement,” the insider added.
As Don Jr. journeys through his budding romance with Bettina Anderson, the world seems eager to know the next move in their relationship, especially given that Guilfoyle will remain an influential figure within the Trump camp. The inauguration weekend provided a major glimpse into the evolving dynamics of their relationships, with all eyes watching closely.
