Donald Trump Jr., 48, and Kimberly Guilfoyle, 57, have had zero contact since ending their engagement last year.
A source said that the former couple has maintained complete radio silence since their 2024 split, even as Guilfoyle continued working within the Trump administration until her abrupt departure this week. The same source emphasized that the breakup was neither “nasty” nor “bitter,” describing it instead as an amicable parting of ways.
The disclosure about their nonexistent communication arrives one day after President Donald Trump, 80, publicly minimized his connection to his son’s former fiancée. Speaking to reporters, the president made clear that Guilfoyle was never considered family.
That presidential distancing preceded Guilfoyle’s resignation Tuesday from her post as U.S. Ambassador to Greece. Trump had asked her to step down following allegations that she pressed political donors to cover personal expenses. Guilfoyle denied the accusations and pledged to “vigorously defend” herself against them.
The couple’s romantic history stretches back to 2018, when they began dating following Guilfoyle’s departure from Fox News. They announced their engagement in 2020, creating a high-profile political partnership that frequently placed them at the center of Trump-world social events.
By December 2024, the outlet had exclusively reported the relationship’s end after nearly six years together. “Don and Kimberly haven’t been getting along over the past year,” one source told the outlet at that time. “They get argumentative at Mar-a-Lago in front of people. Nothing crazy, but you know when a couple is fighting. They bicker in public.”
Even before the split became public, Trump Jr. Had been spotted repeatedly with Palm Beach socialite Bettina Anderson, 39. The new relationship progressed quickly, and by May the pair married in an intimate ceremony on a private island in the Bahamas.
Approximately 40 guests witnessed the vows, including Trump Jr.’s five children from his previous marriage to Vanessa Trump. The president himself was notably absent, claiming online that “circumstances pertaining to Government, and my love for the United States of America” prevented his attendance.
Meanwhile, Guilfoyle’s future plans appear to involve leaving both Washington and her former life behind entirely. An insider said that she intends to find a “rich husband in Europe,” signaling a dramatic geographic and social reinvention.
The rapid sequence of events — from administration exile to presidential disavowal to the revelation of complete estrangement from her former partner — marks a striking fall for Guilfoyle, who once occupied a central place in the Trump family’s inner circle. Her defiant message upon resigning suggested fight remains, even as her position collapsed around her.
Trump Jr.’s new marriage and continued proximity to his father stand in sharp contrast to Guilfoyle’s isolated position, professionally severed and personally disconnected from the world she inhabited for six years.