Considering just how many red flags there were in Kimberly Guilfoyle and Donald Trump Jr.’s relationship that we couldn’t ignore, most people weren’t utterly shocked by the pair’s breakup nearly a year ago. While the couple never making it to the altar was predictable, there was still plenty of mystery surrounding the split. Looking back, though, it seems like Don Jr. no longer found Guilfoyle to be a compatible partner.
Guilfoyle and Don Jr. started dating in 2018 before getting engaged in 2020. News that they called it quits came to light in December 2024. And, if you thought that timing was suspicious, you were right. A source told Us Weekly, “Don and Kimberly broke up before the election and started to divide assets around the end of September,” but they reportedly kept things quiet until after Election Day to avoid stealing focus from Don Jr.’s dad. While the source said that the relationship ended on good terms, it was reportedly Don Jr. who initiated the breakup. “Kimberly and I will never stop caring for each other and will always keep a special bond,” he told Page Six after news broke that they had parted ways. He also expressed happiness that Donald Trump had given her the role of U.S. ambassador to Greece. While Don Jr. had nothing but nice things to say about Guilfoyle publicly, things may not have been so lovey-dovey behind closed doors.
Days before his split from Kimberly Guilfoyle was confirmed, Donald Trump Jr. was photographed holding hands with his now-girlfriend, socialite Bettina Anderson. This fueled rumors that Don Jr. ditched Guilfoyle for his alleged mistress. And, he may have thought Anderson was a better match for some harsh reasons. “Don Jr. has always wanted to look good in his father’s eyes,” an insider told People, noting, “Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress him.” And, apparently, Guilfoyle’s notoriously tacky closet made matters worse. “Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual,” a source explained, adding, “The tight dresses need to go and she has been told that.”
