5 Signs Kimberly Guilfoyle & Donald Trump Jr.'s Relationship Is On The Rocks

Donald Trump Jr. and Kimberly Guilfoyle have been in a high-profile relationship for over half a decade now, and they have been engaged since late 2020. At times they have been surprisingly private (news of their engagement didn't break until about a year after the initial proposal), but overall they have been incredibly open about their love for one another — and that's why close observers have now begun to wonder if there is trouble in paradise. 

Guilfoyle was once a Fox News presenter, but she left the network in the wake of misconduct allegations and has been working independently and with the Trumps ever since. Her career, as well as her reliance on her fiancé's family for fame, makes Guilfoyle's sudden diminished media presence all the more noticeable and meaningful, but that is hardly the only signal that Kimberly Guilfoyle and Donald Trump Jr.'s relationship isn't going to last. There are quite a few signs that this political power couple is on the fast track to Splitsville.

Donald Trump Jr. and Kimberly Guilfoyle seem to love sharing every moment of their love story on their social media, which made this July 4, 2024, stand out for the wrong reasons. 

Guilfoyle's activity on the Fourth was minimal, and she only posted a somewhat generically patriotic quote from Donald Trump Sr. on X, formerly known as Twitter. On the other hand, Donald Trump Jr. posted a series of videos on Instagram featuring him and a few children setting off fireworks while he smoked a cigar. But to the surprise of many, Kimberly Guilfoyle was nowhere to be seen in any of the clips. 

For the average couple, a single missed (or at least not posted) holiday might not be cause for alarm, but given that both Guilfoyle and Trump are very open about their relationship and very politically active and motivated, skipping Independence Day overtures online could be a bad sign.

Kimberly Guilfoyle certainly can't be called camera shy, and she typically enjoys sharing her exploits with Donald Trump Jr. as well as her in-and-out daily activities on social media. Or at least, she did enjoy it. 

Guilfoyle's Instagram has been bursting with content for years, and it was rare for the conservative media personality to go more than a few days without posting some new political statement, personal pictures, or event photos. However, as of this writing, Guilfoyle hasn't posted anything new to her page since June 20, 2024, meaning that she has taken a more than two-week break from sharing her exploits with the public, and she still surprisingly remained silent even on the Fourth of July holiday.

Although this conspicuous absence doesn't necessarily mean that she's dealing with love troubles specifically, considering that it wasn't uncommon for her to make multiple social media posts in a day, her sudden silence likely means something's up.

Kimberly Guilfoyle has made a habit out of sucking up to Donald Trump Sr., and while the former president definitely seems to enjoy adoration, Guilfoyle's outspoken encouragement of her maybe-future-father-in-law could actually be a bad omen for her relationship with the younger Donald. 

Guilfoyle has made a career out of conservative punditry, and no right-wing star is more bankable than Donald Trump. So then, is it just a coincidence that she began a romance with Don Jr.?

One would hope that any engagement or marriage starts with pure and loving intentions, but if Guilfoyle is more enamored with the idea of gaining the surname Trump or becoming a part of the Trump brand than she is with Donald Trump Jr.  himself, it will undoubtedly spell trouble for the longevity of their union. And, even if Guilfoyle truly loves Donald Jr. for him, the fact that their love lives and professional lives are so intertwined will make their liaison more difficult than average.

Kimberly Guilfoyle has been an ardent supporter of Donald Trump's political career for years, but rumor has it that the Trump family really doesn't like Guilfoyle all that much. When asked about the supposed familial divide, Eric Trump told Page Six that he "completely disagree[s] with the narrative and happen[s] to think the world of Kimberly." However, other insiders around the Trumps seem to agree that Guilfoyle hasn't blended well into the clan, no matter how hard she may be trying.

Pillars of the Trump brood like Melania, Ivanka, and Donald Trump Sr. himself have reportedly had their issues with Guilfoyle, which could understandably be causing issues between Kimberly and her fiancé. It's hard enough in an average family when someone's significant other doesn't quite fit in, and that is probably magnified a hundredfold within a super-famous, oftentimes unpredictable tribe like the Trumps.

Although the news of their engagement broke in January 2022, Donald Trump Jr. reportedly proposed to Kimberly Guilfoyle in December 2020. In the grand scheme of things, a four-and-a-half-year-long engagement period isn't the longest time imaginable, but considering that Donald Jr. began dating Kimberly in 2018, this could be a pretty bad sign. Every couple obviously likes to move at their own pace, but Guilfoyle and Trump have now been engaged for quite a bit longer than they dated before they got engaged in the first place, which makes it seem like one or both of them have pumped the brakes on a relationship that was previously going at a pretty quick pace. 

However, in fairness to them, the past few years have been astoundingly busy for the Trump family, and they may just be waiting until Trump Sr. has enough time between court dates to make it to a wedding. Or, given that they kept their engagement a secret for over a year, it's not beyond belief that the couple is already married and just hasn't announced it yet!