Fans following Kimberly Guilfoyle on Instagram started to notice a pattern in her posts that hinted at a split with Donald Trump Jr. On July 18, 2024 Guilfoyle uploaded a photo carousel from her time speaking at the Republican National Convention, but her political punditry was not of great concern to some followers. “Is she still with Donald jr? He seemed distant to her,” an Instagram follower wrote. Oddly, Guilfoyle and Trump Jr.’s realtor decided to declare the couple were not broken up. “[Y]es and they are very happy,” Rob Thompson, the realtor who helped the pair close a deal on their home responded.
Ever since that RNC post, Guilfoyle’s uploads became increasingly impersonal as she focused more on heavily posting and resharing posts from her potential future father-in-law, Donald Trump. However, during that time, Guilfoyle appeared to desperately try and squash break up rumors by posting a quick gif of her and Donald Jr. hugging to her Instagram Stories on July 24.
Despite the quick Don Jr. post to her Instagram stories, scrolling through her page made it clear Guilfoyle had changed how she posted. She used to frequently upload snaps and selfies alongside her fiancé, but Junior had been absent from her feed since July 12 when Guilfoyle posted pics from a Trump rally. Guilfoyle has since taken to posting memes instead of looks at her personal life. Besides the lack of photos together, fans also pointed out how the couple’s wedding engagement could be in trouble.
Did Kimberly Guilfoyle and Don Jr. ever plan on actually getting married?
As rumors of Kimberly Guilfoyle and Donald Trump Jr.’s break up swirled, one person pointed out that the couple seemed to be dragging their feet on walking down the aisle together. The pair took their time going public with their engagement, as Guilfoyle officially announced it on Instagram in a touching post in February 2022. Reportedly, Trump had popped the question over a year earlier on New Year’s Eve 2020. “Why haven’t Don jr & his fiance married yet?” a person asked on X, formerly Twitter, in August. “Almost FIVE YRS.engaged! What’s the holdup?” they added.
Besides the length of their engagement, Guilfoyle and Trump made anniversary posts celebrating six years together that raised eyebrows. While the former “The Five” host gushed over her beau in an April 2024 Instagram post, Trump took a seemingly odd approach to showing his love. “@kimberlyguilfoyle thanks for always being there no matter what the haters are throwing our way. I love you,” he wrote in the caption of his post. A few followers pointed out that the two did not exactly look ready to tie the knot. “What an uncomfortable looking couple,” an Instagram user commented.
The protracted engagement had come up before whispers of Guilfoyle and Trump’s split had spread. “I already feel married and committed to him, 100 percent,” Guilfoyle said on the “Successful Philanthropy” podcast (via OK!). She made it seem as if there was no rush for their pending nuptials as she repeated her mantra that the two already feel like a married couple.
