Kimberly Guilfoyle, once a prominent fixture at Donald Trump Jr.’s side during campaign rallies and glittering Mar-a-Lago events, is reportedly struggling emotionally after being quietly edged out by the Trump family. The former couple, who began dating in 2018 and got engaged in 2022, abruptly ended their relationship in December 2024.
Sources close to Guilfoyle suggest the split didn’t just sever her bond with Trump Jr., but also effectively ended her place within the inner circle of the Trump family. “She gave them everything — her time, her energy, her loyalty. But the second Don moved on, so did the family. Kimberly was discarded like yesterday’s news,” one insider told RadarOnline.
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The wound reportedly deepened when Trump Jr. introduced his new girlfriend, Palm Beach socialite Bettina Anderson, at a Trump family event, where Anderson was warmly embraced. “They never embraced Kimberly like this,” the source added. “Bettina fits their polished image. Kimberly never quite made the cut.”
Despite the professional success Guilfoyle has achieved—including her current role as U.S. Ambassador to Greece—sources say she is privately grappling with feelings of rejection and emotional loss. A friend confided to columnist Rob Shuter: “Kimberly’s putting on a brave face. But behind the scenes, it hurts. She went from nearly being a Trump to being totally iced out.”
Though the romance has ended, Guilfoyle reportedly hasn’t given up entirely on maintaining a personal connection with Trump Jr. In January, a source told Page Six: “She has every intention of maintaining a relationship with Donald Trump Jr. Kimberly and Don have known each other for years and have a lot of history together, so she feels like they’ll always have a connection.”
That dynamic was put to the test during the recent presidential inauguration events for Donald Trump, where Guilfoyle encountered her ex and his new partner. According to People, the atmosphere remained civil, but Guilfoyle remained visibly aware of the situation.
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“Kim saw Don with Bettina, and it was all civil. No negativity,” a source noted, adding that Guilfoyle kept a “watchful eye.” Despite the personal fallout, both parties have maintained a respectful public tone. After Guilfoyle’s diplomatic appointment, Trump Jr. expressed his support, saying:
“I could not be more proud of her and the important role she’ll continue to play in my father’s administration.” Though her relationship with Trump Jr. has ended, Guilfoyle’s political star continues to rise—albeit without the family ties she once seemed destined to solidify.
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