Donald Trump Jr and Kimberly Guilfoyle parted ways without any public animosity and Don Jr sill has a framed photo of his ex-fiancee on a rack in his room. The duo broke up around the election, but it only became public after President Donald Trump named Guilfoyle Greece’s ambassador, sending her far away from Florida. A few days before that, Don Jr was seen with Palm Beach socialite Bettina Anderson, but it was not official. Eventually, the break up became official, though neither Donald Trump Jr nor Guilfoyle shed any light on why they broke up.
As they maintained civility in public on several occasions that they met, Donald Trump Jr accidentally revealed his framed photo with Guilfpyle as he was speaking over a video call at the DC Blockchain Summit 2025. The keen eyes of social media users quickly pointed out that one of the photos on a rack in Don Jr’s background is that of the former couple.
The photo is from an anniversary celebration of Don Jr and Guilfoyle, taken in 2021. Guilfoyle’s Instagram account still has the photo as neither of them removed any photo from their respective accounts.
Trump Jr and Guilfoyle began dating in 2018 after Trump Jr’s divorce from Vanessa Trump. Guilfoyle was working with Fox News at that time. The same year, she left the channel and joined Trump’s re-election campaign. Don Jr and Guilfoyle got engaged in 2020 but it was called off unceremoniously as Don Jr started seeing Anderson. Insiders claimed Guilfoyle was not liked by the Trump family because of her conduct, her dressing etc though similar claims were made about Bettina Anderson that she was not welcome in the Trump family. However, both Bettina and Anderson move freely in Trump’s inner circle.
Vanessa Trump was recently in the news as Tiger Woods confirmed dating Donald Trump Jr’s ex-wife.
