All The Reasons Trump Supposedly Doesn't Like Kimberly Guilfoyle

Kimberly Guilfoyle has made it abundantly clear that she's her future-father-in-law's biggest fan (or at least one of them), but if you've found yourself wondering if Donald Trump is as enamored with her, well, you're not alone. In fact, there have been a few reports to suggest the businessman isn't a Guilfoyle stan for a number of reasons. 

Tension in Donald and Guilfoyle's relationship is said to have begun right from the start. Speaking to The Atlantic of the very first time she joined the family at an official event back in 2018, an insider claimed that the president was unimpressed by the amount of attention she got. That wasn't his only gripe, though. Another thing Donald seemed to take issue with was his view of Guilfoyle as an "airhead." This was despite her past as an attorney. However, one especially ick-inducing possibility for the disapproval stemmed from Donald's own interest in her. As one advisor told the outlet, the elder Donald actually did like Guilfoyle. But, like, liked liked her. Granted, Donald has said some eyebrow-raising things about his own daughter, Ivanka Trump, so maybe the fact that his son ended up dating someone he's said to have inquired about isn't all that big of a deal. 

Whatever the root of the awkwardness, more than one source told The Atlantic that Guilfoyle ended up being scratched off the list for that year's Thanksgiving celebration at Mar-a-Lago. Of course, Donald Trump Jr.'s rep denied that was the case, so perhaps there was a miscommunication there. However, we took a look through Guilfoyle's Instagram, and she certainly didn't post about being part of any of the Florida festivities. 

Whether Guilfoyle was invited to Thanksgiving 2018 with the Trump family or not, rumors of awkward vibes have continued — and it turns out Guilfoyle and Donald's relationship is reportedly more complicated than many may realize. This is thanks in no small part to Guilfoyle's work on Eric Greitens' Senate campaign in 2021. Speaking to Politico, one insider claimed, "Trump thinks Greitens is problematic, and that Kim is annoying ... He said, 'Why the f*** is she working for him?'" Yikes.

Greitens ultimately lost his bid for the Senate, and Guilfoyle went on to take up a very active role in her fiancé's father's campaign. In fact, even as she and Donald Trump Jr. have struggled to squash split rumors, Guilfoyle was actually the only member of Donald's family to join him for the premiere of "The Man You Don't Know" documentary. Not only that, but she also made a solo appearance (and spoke) at another MAGA-related premiere that took place at Mar-a-Lago a day later, "A Line in the Sand." She did seem to confuse Mar-a-Lago for the nightclub with her outfit choices at both events, but that's beside the point. 

Perhaps Donald warmed up to Guilfoyle during his third campaign for the presidency, or maybe he even felt bad for seemingly confirming that she gave him the ick at the 2024 Republican National Convention. Either way, it certainly seems as though Donald and Guilfoyle are keen to allay any concerns that the reality star-turned-politician doesn't like his prospective daughter-in-law.