Sad Details About Kimberly Guilfoyle's Life Since She Broke Up With Donald Trump Jr.

Kimberly Guilfoyle's tragic life has only gotten sadder since her split from Donald Trump Jr. in 2024. In September 2025, the former Fox News anchor lost her close friend, Charlie Kirk, after he was fatally shot while debating students at Utah Valley University. Shortly after news of the 31-year-old conservative commentator's passing broke, Guilfoyle penned a personal tribute to him on Instagram, sharing a carousel of photos of them over the years. 

"I will miss my dear friend, Charlie Kirk. Charlie had such a big heart and a powerful presence." Guilfoyle wrote. While praising Kirk's contributions to political discourse, she also extended her condolences to his two kids and his wife, Erika, whose last Instagram post with him was so tragic after his passing. However, Guilfoyle already seemed to be going through tough times before Kirk's passing. An Instagram post from earlier in September 2025 caught people's attention, leading them to believe that she had undergone additional plastic surgery. However, that wasn't the only noteworthy aspect of the photo, as Guilfoyle was all dressed up in a loosely fitted dress and a leather jacket, which was a stark departure from her normal body-hugging dresses. 

According to a People's insider account from December 2024, Don Jr. wasn't a huge fan of his partner's decision to wear tightly fitted dresses because they made her seem overly formal at every event. It's plausible that her ex's criticism got to her a bit, and she sought to prove him wrong by donning conservative clothing and undergoing another MAGA makeover. However, that's not the only sign that Don Jr.'s former fiancée is having an identity crisis.

Kimberly Guilfoyle's social media behavior in 2025 hinted that she was lost without Donald Trump Jr. Her confusing Instagram posts gave the impression that she was struggling to figure out who she was after the end of her long-term relationship. At several points, she praised Donald Trump Sr. through her Instagram posts. However, in the middle of these politically charged posts, she would throw in a random photo of herself in an itty-bitty dress. 

Things got even more muddled when the former Fox News anchor mixed in a cooking video with everything else. Although Guilfoyle's mishmashed social media behavior could be her way of telling the world how she was coping just fine after the public split, her posts only had the opposite effect. In fact, even Guilfoyle's Instagram tribute for Donald Trump Jr.'s birthday served as a heartbreaking reminder that she couldn't let go. 

Instead of just writing a simple Happy Birthday as most amicable exes who were in the public eye would have, Guilfoyle went all out and shared an Instagram Story featuring a collage of images of herself clinging to Don Jr. A few days later, in January 2025, Guilfoyle used Eric Trump's birthday to desperately remind Don Jr. of happier times together. She made the strange decision to share an Instagram Story featuring a snap of herself and Don Jr. posing with kids while the birthday boy himself was at the very edge of the photo. Here's hoping that Guilfoyle's life turns around.