Donald Trump Jr. is engaged again, but his ex-fiancée isn’t buying it.
President Donald Trump announced his eldest son’s engagement to Palm Beach, Florida, socialite Bettina Anderson at a White House holiday party on December 15, 2025. The news comes about a year after Trump Jr.’s previous engagement to Kimberly Guilfoyle fell apart.
Guilfoyle, 56, now serves as the U.S. ambassador to Greece. But sources say she has major concerns about her ex’s new relationship.
According to People magazine, Guilfoyle doesn’t think Anderson, 39, is the right match for the 47-year-old Trump Jr. A source said Guilfoyle feels Anderson is more interested in the attention that comes with being connected to the Trump family than in Trump Jr. himself. The same source also said Guilfoyle doesn’t believe the relationship will last.
Trump Jr. and Guilfoyle dated for six years. They got engaged in 2020 but never made it to the altar. Reports surfaced in December 2024 that Trump Jr. had been seeing Anderson for about six months while still technically engaged to Guilfoyle.
Sources told Page Six at the time that Guilfoyle was not happy about the split. The former couple had reportedly been arguing at Mar-a-Lago in front of other people.
At the White House Christmas party, Trump Jr. spoke to guests about the proposal. “It’s not often that I’m at a loss for words because we usually do the ranting and raving really well, but this is a little different,” he said. He thanked Anderson for that one word, “yes,” and called the engagement “a big win for the end of the year.”
Anderson also spoke at the event. She called Trump Jr. “the love of my life” and said she felt like “the luckiest girl in the world.”
This is Trump Jr.’s third engagement. He was married to Vanessa Kay Haydon from 2005 to 2018. They have five children together: Kai, 18; Donald III, 16; Tristan, 14; Spencer, 13; and Chloe, 11. Vanessa filed for divorce in 2018, and Trump Jr. started dating Guilfoyle that same year.
Anderson comes from a wealthy Palm Beach family. Her late father, Harry Loy Anderson Jr., became the youngest bank president in the country at age 26 when he took over Worth Avenue National Bank. Her mother, Inger Anderson, is a well-known philanthropist in Palm Beach.
Anderson graduated from Columbia University in 2009 with a degree in art history. She has worked as a model and appeared in Palm Beach Illustrated. In 2005, she and her brothers started The Paradise Fund, a nonprofit focused on protecting Florida’s environment.
On Instagram, Anderson jokes that she’s “just your typical stay-at-home mom… only I don’t do household chores… or have a husband… or have kids.”
The couple was first spotted together in August 2024 at a Palm Beach restaurant. Anderson attended the Republican National Convention that summer, sitting near Trump Jr. and Guilfoyle. She and Trump Jr. went public as a couple at President Trump’s inauguration in January 2025.
Sources say the breakup between Trump Jr. and Guilfoyle wasn’t clean. People magazine reported that until recently, the two still had belongings at each other’s homes.
Guilfoyle moved to Athens after being confirmed as ambassador to Greece in September 2025. President Trump nominated her for the role in December 2024, around the time her relationship with his son ended.
Anderson’s family regularly visits Mar-a-Lago, and she helped host a Trump campaign fundraiser there in October 2024. The couple has since attended many White House events together and joined the president on a trip to Scotland in July 2025.
