Donald Trump Jr. found himself in an uncomfortable situation during his father’s pre-inauguration events when both his ex-fiancée, Kimberly Guilfoyle, and his new girlfriend, a Palm Beach socialite, attended the same functions. Trump Jr. and his new girlfriend were seen at a ball on Friday, which was also attended by his ex. The three were later photographed together at President-elect Donald Trump’s candlelight dinner at the National Building Museum on Sunday.
Guilfoyle, who was in a relationship with Trump Jr. from 2018 to 2024, continues to have a professional connection with the incoming administration. President Trump has appointed her as the U.S. Ambassador to Greece.
Meanwhile, Trump Jr.’s new girlfriend, who has been dating him for several months, is relatively new to the MAGA scene.
Photo: Katherine Lugo/Instagram
Sources shared that despite the awkwardness, Guilfoyle and Trump Jr. have managed to maintain a cordial relationship. However, their breakup in 2024 was reportedly marked by occasional arguments. “They bicker in public,” one source commented, noting their ongoing tension. The new couple, Trump Jr. and his girlfriend, are said to be very happy together, with another insider describing them as a natural fit.
Despite their happiness, some within the Trump family are reportedly not pleased with Trump Jr.’s relationship due to his girlfriend’s liberal-leaning past. As inauguration events continue, Guilfoyle is expected to be seated near Trump Jr. and his new girlfriend during the official ceremonies on Monday, adding to the already tense family dynamics.
