Donald Trump Jr’s ex, Kimberly Guilfoyle, is reportedly coming to terms with his engagement to socialite Bettina Anderson, though she has lingering doubts about the relationship.
Guilfoyle, 56, who was with Trump Jr for six years, is said to want the best for him but questions whether Anderson, 39, is truly committed to the former president’s son or attracted to the status that comes with the Trump name.
Public Announcement Adds Pressure
Trump Jr., 47, made the engagement official during a White House Christmas reception, a setting that reportedly intensified Guilfoyle’s unease.
A source told People that seeing the announcement unfold publicly “only added to her doubts about the relationship.”
Despite the breakup, the former couple remains close, though they had only recently fully separated their living arrangements.
The White House Proposal
During the festive event, Trump Jr took the microphone after embracing his father and joked about his uncertainty, saying, “You’re trying to ask, and you’re not sure what the answer’s gonna be.
But she said yes, which is a big win for the end of the year.”
Bettina Anderson, beaming in a red strapless gown, thanked the president and First Lady Melania Trump, calling the engagement “the most unforgettable weekend” of her life.
President Trump offered her a kiss and whispered “good luck” as the audience applauded.
A Ring Fit for a Socialite
Forbes later reported that Anderson’s engagement ring is an eight-carat emerald-cut diamond crafted by Dallas jeweler Sue Gragg of Sue Gragg Precious Jewels.
Experts speculated the ring could be even larger and more valuable than the one Trump Jr. gave Guilfoyle in 2022.
A Relationship in the Spotlight
Trump Jr. and Anderson’s romance reportedly began in spring 2024, while he was still publicly linked to Guilfoyle.
By September, DailyMail.com obtained photos showing the couple sharing intimate moments at a Palm Beach restaurant.
The pair frequently attended high-profile events in 2025, including the Super Bowl in New Orleans and President Trump’s March address to Congress, signaling their integration into Trump Jr.’s social and political circles.
Anderson’s Palm Beach Roots
Bettina Anderson comes from one of Palm Beach’s old-money banking families.
Her father, Harry Loy Anderson Jr., known as H. Loy, led several financial institutions over decades, while her mother, Inger, immigrated from Sweden.
Her presence at official White House dinners, including one honoring Saudi Arabia, has cemented her position in the Trump family’s inner circle.
Moving Forward
Guilfoyle has not publicly commented on the engagement.
Meanwhile, Trump Jr., who was previously married to Vanessa Trump from 2005 to 2018, appears committed to Anderson.
Sources note that the couple’s social appearances and family interactions indicate a serious relationship, though some insiders caution that public scrutiny and family dynamics may continue to test the new couple’s bond.
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