Kimberly Guilfoyle's Tribute To Charlie Kirk Put Her Relationship With Don Jr. On Blast
The assassination of Charlie Kirk — heartbreakingly witnessed by his wife and children — is being mourned worldwide. Even people who disagreed with the conservative influencer's beliefs and messaging condemned the senselessness of his murder. The president and his inner circle were particularly affected; many knew Kirk personally, and his Turning Point USA initiative helped bring young right-leaning voters to the polls in 2024. Donald Trump ordered official flags lowered to half-mast for several days, and he will be one of the key speakers at a memorial service for Kirk in Glendale, AZ, on September 21. Among the most deeply grieved by Kirk's death was Kimberly Guilfoyle, who transformed herself from a left-leaning attorney to an ultra-MAGA loyalist. She has posted a number of tributes to "my dear friend" on her Instagram account. One stated, "Charlie had such a big heart and a powerful presence. He loved this country, stood for freedom, and inspired so many with his courage and conviction."
But in the process of memorializing her friend, Guilfoyle also revealed her biggest insecurity. Two of her social media tributes are slideshows of her personal memories with Kirk — and the majority of them include her former fiancé, Donald Trump Jr. They could even be considered a timeline of the former power couple's relationship; some of the pics show the first son clean-shaven, which would have been in the very early days of their romance, while others would have been taken after 2019, when Don Jr. first grew the beard he still sports today. Combining a life cut short with a high-profile relationship gone sour makes these memories all the more poignant.
Guilfoyle can't let go of the past
It can be hard to accept that a flame has lost that lovin' feeling, especially when the romance lasted as long as the one between Kimberly Guilfoyle and Donald Trump Jr. The couple had known each other for years before officially starting to date, and their engagement lasted nearly five years before they called it quits. This was sad enough, but the reason was even more humiliating: Don Jr. and Guilfoyle broke up because he'd found Bettina Anderson, a younger woman who was reportedly a better fit for the Trump family image. Yet Guilfoyle's social media shows she can't quit her exes, no matter how much distance they try to put between themselves and her.
Through her photo carousels, the incumbent U.S. ambassador to Greece prominently defined herself as Don Jr.'s ex as much as she was Charlie Kirk's friend. The first son wasn't as generous. Though Don Jr. posted plenty of commentary on the assassination, the one photo collection he shared on Instagram had only one featuring Guilfoyle — and it was a blurry crowd shot with his then-fiancée looking over his shoulder. More significantly, Don Jr. also included a Kirk pic from a festive event which featured Anderson, along with his oldest son Donnie. The message was subtle but undeniable: I've moved on.
Ironically, one of Charlie Kirk's last Instagram posts urged single followers to "get married and have kids. You won't regret it." Yet two of his good friends were both divorced and opted not to make it to the altar themselves. We'll never know what Kirk might have thought about their breakup or their post-split social media messages.