Kimberly Guilfoyle 'still very fond' of Donald Trump Jr. at inauguration event

Donald Trump Jr. found himself navigating complex relationships during his father's inauguration events. At various gatherings surrounding President Trump's swearing-in ceremony, Don Jr. was seen with both his new girlfriend, Bettina Anderson, and his former fiancée, Kimberly Guilfoyle.

Despite the apparent awkwardness, sources told PEOPLE magazine there was no drama between the three, with Guilfoyle and Don Jr. remaining civil throughout the weekend.

According to an attendee, Guilfoyle, who is expected to be appointed as U.S. Ambassador to Greece, appeared to have accepted the situation, even though she was still fond of Don Jr. and kept an eye on him and Anderson.

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

Don Jr. and Guilfoyle had been engaged since December 2020, but the couple's relationship ended just weeks after the 2024 election. Shortly after their breakup, Don Jr. was seen with Anderson, a Palm Beach model and socialite. The timing of their split coincided with Guilfoyle's nomination for the ambassador position.

Despite the change in relationships, the two have reportedly remained friends, with Guilfoyle continuing her support of the Trump family.

Anderson, who is described as confident, sassy, and comfortable in the spotlight, is reportedly eager to fit into the Trump family's world. While she may not have the political experience of Guilfoyle, who has been a strong Trump ally, Anderson is said to be interested in finding a role within the Trump administration.

Despite her lack of political experience, insiders believe she may eventually find her niche in the family’s political circle.