President Trump may be one of the most popular presidents in the world right now. However, it is often his children and their highly publicized personal and professional controversies that keep the family in the spotlight. For instance, his eldest son, Donald Trump Jr, created quite a buzz when his engagement with media personality Kimberly Guilfoyle was called off.
The former couple began dating in 2018 and were engaged for several years, but they abruptly split in 2024, and Don Jr. has since moved on with Florida socialite Bettina Anderson. As of 2025, the couple is engaged, as Don finally popped the question with an 8-carat ring, making the 39-year-old Anderson the likely next Mrs. Don Jr.
According to The List, Trump Jr. had been seen with Palm Beach socialite Bettina Anderson before news of his breakup became public in MAGA circles.
While Kimberly embraced her new role as U.S. ambassador to Greece and showed the world that she has moved on, many critics saw this as a tactic to keep her away from the MAGA crowd, as she had simmering issues with not one but many members.
Bettina Anderson showcases her 8-carat emerald-cut diamond engagement ring from Donald Trump Jr. at a White House event. The flawless D-color gem, designed by Sue Gragg.#bettinaanderson #donaldtrumpjr #engagement #ring #diamond pic.twitter.com/LdFJhxG5mc
— Heading (@HeadingDaily) December 17, 2025
Moreover, despite Guilfoyle attempting to start fresh in Greece, sources reveal that certain things from the past continue to trouble her. For instance, the mansion, which Don Jr. and Kimberly Guilfoyle own together, now has a new visitor. It’s none other than Bettina, who reportedly visits the place with her fiancé.
“The last thing she wants is to see Bettina using something she owns,” a source told the outlet. Although Guilfoyle’s social media posts reveal that she may have moved on, she remains uneasy about her personal belongings being used by her ex’s new partner, a source told the outlet.
However, despite all the drama, Guilfoyle has shown a professional attitude in public and attended several public events, including the inauguration, where Donald Trump Jr.’s new girlfriend, Bettina Anderson, was present.
Surprisingly, Guilfoyle’s tensions aren’t limited to Don Jr. or his better half, as she reportedly has issues with Lara Trump. A former Trump campaign official told the Daily Mail that Guilfoyle “speaks very badly about Lara Trump” and was upset when Lara was appointed co-chair of the Republican National Committee in March 2024.
Dumbest Trump Lara and Kimberly Guilfoyle, Don Jr’s girlfriend, are hosting an online Women For Trump Empower Hour. Followed by Hair Extensions For Trump, Women Who Hate Themselves For Trump, and Women Who Date Or Marry Trumps And Are Getting 18K A Month As Campaign Advisors pic.twitter.com/kry0gD2wM6
— Paul Rudnick (@PaulRudnickNY) May 21, 2020
Even though people did not know if Kimberly Guilfoyle and Lara Trump were friends, recent reports suggest that the relations between the two have improved, with no visible public feud.
While the Greek ambassador had acknowledged Lara’s birthday on Instagram, there have been signs of tension, including moments when Lara and Trump attorney Alina Habba appeared to leave Guilfoyle out.
Furthermore, the media personality was also kept on the sidelines during her swearing-in ceremony, as ambassadors to India and Ireland appeared to receive greater media attention. Several other high-profile officials from the Trump administration also attended the event.
Don’t be so disrespectful.
Kimberly Guilfoyle @kimguilfoyle did a lot to support President Trump and his campaign and she and @DonaldJTrumpJr are on good terms. The media loves sensationalizing things. Don Jr even congratulated Kimberly on her appointment today.
She will be a… https://t.co/eApWvJDqwL pic.twitter.com/ABwQ2viXpw
— Laura Loomer (@LauraLoomer) December 11, 2024
On the work front, according to Greek City Times, Guilfoyle told reporters in October that Greece is “a cornerstone of stability in the Eastern Mediterranean.”
The former Fox News host aspires to strengthen political ties between America and Greece, thereby expanding the existing relationships in the agriculture, tourism, and shipping sectors.
What a pleasure speaking at @AmChamGr‘s Greek Economic Summit in Athens today! The U.S.–Greece partnership is entering a new era of economic security and shared prosperity. Together, we’re building resilient supply chains and strengthening a critical alliance. I’m proud of what… pic.twitter.com/g70tASpMFd
— Ambassador Kimberly Guilfoyle (@USAmbassadorGR) December 2, 2025
On November 4, she attended the official Ceremony of the Presentation of Credentials at the Presidential Palace in Athens to speak with Greek President Konstantinos Tasoulas. Her first official public event in Athens was where she hosted her first gala reception at the Zappeion palace alongside the Transatlantic Energy Cooperation Forum, per Parapolitika.
