Don Jr. Caught With Photos of His Ex Kimberly Guilfoyle During Livestream
President Donald Trump’s son doesn’t seem to be completely over ex-fiancée Kimberly Guilfoyle
Donald Trump Jr. revealed in a livestream Wednesday that he still has photos of ex Kimberly Guilfoyle on display.
While speaking over video call at the DC Blockchain Summit 2025, Trump Jr.’s background contained framed photos of him and ex-fiancé Guilfoyle on his shelves.
One of the pictures matches a photo from Guilfoyle’s Instagram in 2021.
Trump Jr. and Guilfoyle began dating in 2018 after his split from Vanessa Trump. That same year, Guilfoyle left Fox News to join President Trump’s re-election campaign.
The two then got engaged in 2020 but reportedly ended their seven-year-long relationship in Dec. 2024, after the eldest Trump was allegedly spotted cozying up with Palm Beach socialite Bettina Anderson.
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A source told People that Trump Jr. and Anderson were seeing each other for six months before going public with their relationship, claiming that Guilfoyle “looked the other way.”
Suspicions were also raised when Don Jr.’s daughter, Kai Trump, posted a photo of “the whole squad” in November, which included the entire Trump family (minus Melania) and Elon Musk, but noticeably not Guilfoyle.
The whole squad pic.twitter.com/5yQVkFiney
— Kai Trump (@kaitrump) November 6, 2024
Though Don Jr. never officially announced his split from Guilfoyle, he has since been spotted with Anderson at multiple events since late last year.
The two recently made an appearance at the amfAR Palm Beach Gala on March 17.
President Trump also nominated Guilfoyle to be ambassador to Greece in December.
The former prosecutor posted on Instagram her speaking at a Greek Independence Day Celebration at the White House Tuesday.
Before Trump Jr., Guilfoyle was married to Governor of California Gavin Newsom for five years. A year after her split with Newsom, she went on to marry businessman Eric Villency, with the pair divorcing in 2009.
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