The Subtle Sign Don Jr. Had A Harder Time With His Kimberly Guilfoyle Split Than He Let On

After months of dropping clues — strategically posing away from each other at political events, spending the holidays apart — Donald Trump Jr. finally confirmed his split from Kimberly Guilfoyle in December 2024. It was sad enough to see their eight-year relationship end so abruptly, but the reason behind the breakup was super awkward: Don Jr. was already seeing the much-younger socialite Bettina Anderson on the side and wanted the freedom to pursue the romance more publicly. But just how clean was the break? The eldest Trump son recently revealed a clue, which somewhat surprisingly indicates that his former fiancée may still be on his mind.

Don Jr. was a guest on a panel of the DC Blockchain Summit in late March 2025. As seen on Rumble, he appeared via video call from his home office in Florida, seated in front of a shelving wall unit. The businessman began by discussing his recent visit to a hurricane disaster site in North Carolina, but sharp-eyed viewers were more interested in what was going on in the background. Prominently placed among the many framed photos on the wall unit was one of Don Jr. and Guilfoyle in happier times. In fact, the former Fox News host posted it on Instagram in April 2021. 

The couple, along with Don Jr.'s younger siblings Eric and Tiffany Trump, attended a special event at the Ocean Reef Club in Key West at the time. That particular weekend also just happened to mark a year since Don Jr. and the future U.S. ambassador to Greece first began dating. "[C]elebrating our anniversary and the beautiful wedding of Robert and Carly Desmond," she sweetly captioned the post. 

It's entirely possible that Donald Trump Jr. just doesn't do much home decorating; after all, he's a busy man. In addition to his position with the Trump Organization, Don Jr. and his brothers are ambassadors for President Donald Trump's crypto company, World Liberty Financial. In between all that, he fits in quality time with new girlfriend Bettina Anderson and his five children. So perhaps Don Jr. didn't realize that his home photo gallery still includes a pic of himself with ex-fiancée Kimberly Guilfoyle. But if he deliberately keeps the photo on display, Don Jr. either has a seldom-seen sentimental side, or else he's trying to show everyone he was serious when he reassured Page Six following their breakup, "Kimberly and I will never stop caring for each other and will always keep a special bond." That "special bond" isn't about to lead to a reconciliation any time soon, though.

The first son has already introduced his new flame to his kids, which is a classic sign of a relationship getting serious. Even before the split with Guilfoyle was publicly announced, Don Jr. brought Anderson to a family gathering also featuring his ex-wife, Vanessa Trump, suggesting that he might have been getting his loved ones' blessing before going public with his new flame. More recently, the socialite and Alina Habba palled around and posted selfies at a Trump Doral golf event, with the former Fox News host nowhere in sight. It would appear Guilfoyle's Team Trump friendships are becoming a thing of the past, and her new post as U.S. ambassador to Greece will take her even further from the inner circle. That snap on the shelf may be the closest Guilfoyle will ever be again to her former fiancé.