Kimberly Guilfoyle and Donald Trump Jr: 5 signs the high-profile relationship is on the rocks

Donald Trump Jr and Kimberly Guilfoyle, engaged since late 2020, are facing speculation about their relationship's stability
PUBLISHED JUL 19, 2024
Kimberly Guilfoyle and Trump Jr have generally been open about their affection for each other (Getty Images)
Kimberly Guilfoyle and Trump Jr have generally been open about their affection for each other (Getty Images)

Troubling signs emerge in Donald Trump Jr and Kimberly Guilfoyle's high-profile romance

NEW YORK, NY - FEBRUARY 13:  Donald Trump Jr. and Kimberly Guilfoyle attend the Zang Toi front row d
Donald Trump Jr and Kimberly Guilfoyle have been in a high-profile relationship for over half a decade (Getty Images)

Donald Trump Jr and Kimberly Guilfoyle have been in a high-profile relationship for over half a decade, and they have been engaged since late 2020. While they have sometimes kept their relationship private — news of their engagement didn't break until about a year after the initial proposal — they have generally been open about their affection for each other. However, close observers are now speculating if there is trouble in paradise. Guilfoyle, a former Fox News presenter, left the network following misconduct allegations and has since been working independently and with the Trump family. Her close connection with the Trumps makes her sudden diminished media presence even more noticeable. This is just one of several signs that the relationship between Guilfoyle and Trump Jr may be on rocky ground.

1. Donald Trump Jr's social media posts lack Kimberly Guilfoyle's presence

NEW YORK, NY - FEBRUARY 13: Donald Trump Jr. and Kimberly Guilfoyle pose backstage Gallery II in Spr
Donald Trump Jr's social media posts lack Kimberly Guilfoyle's presence (Getty Images)

Donald Trump Jr and Kimberly Guilfoyle have a habit of sharing their love story on social media, which made this past July 4th stand out for all the wrong reasons. On Independence Day, Guilfoyle's activity was minimal; she only posted a somewhat generically patriotic quote from Donald Trump on X. Meanwhile, Trump Jr shared a series of Instagram videos showing him and a few children setting off fireworks while he smoked a cigar. Notably, Guilfoyle was absent from these clips. For most couples, a single missed or unposted holiday might not be significant. However, given that both Guilfoyle and Trump are very public about their relationship and are politically active, skipping Independence Day celebrations online could be a bad sign.

2. Kimberly Guilfoyle's noticeable absence from Instagram

WASHINGTON, DC - AUGUST 24: Kimberly Guilfoyle walks on stage before pre-recording her address to th
Kimberly Guilfoyle's noticeable absence from Instagram has garnered attention (Getty Images)

Kimberly Guilfoyle is not one to shy away from the camera. She typically enjoys sharing her exploits with Donald Trump Jr and her daily activities on social media. However, this has recently changed. Guilfoyle's Instagram was previously filled with content, and it was rare for her to go more than a few days without posting a new political statement, personal picture, or event photo. Since June 20, she hasn't posted anything new, taking a more than two-week break from sharing her life with the public. Her silence on social media continued even through the Fourth of July. While this absence doesn't necessarily indicate love troubles, considering her usual frequent posts, it suggests something significant might be up.

3. Kimberly Guilfoyle's potentially excessive focus on Trump family

WASHINGTON, DC - NOVEMBER 28: (R-L) Eric Trump, Donald Trump Jr. with his girlfriend Kimberly Guilfo
Kimberly Guilfoyle's potentially excessive focus on the Trump family (Getty Images)

Kimberly Guilfoyle has been very vocal in her support of Donald Trump, and while the former president appreciates adoration, Guilfoyle's encouragement might be a bad omen for her relationship with Donald Trump Jr. Guilfoyle has made a career out of conservative punditry, with no right-wing figure more influential than Trump. Her romance with Trump Jr raises questions about her intentions. One would hope any engagement or marriage starts with pure intentions, but if Guilfoyle is more interested in gaining the Trump surname or brand association than in Trump Jr himself, it could spell trouble for their union. Even if she truly loves Trump Jr, the intertwining of their professional and personal lives adds pressure to their relationship.

4. Rumored dislike of Kimberly Guilfoyle among Trump family members

WASHINGTON, DC - AUGUST 27: U.S. President Donald Trump (C) reacts as he stands with his family memb
Rumored dislike of Kimberly Guilfoyle among Trump family members (L87Getty Images)

Despite her support for Donald Trump's political career, rumors suggest that the Trump family isn't particularly fond of Kimberly Guilfoyle. Eric Trump, in an interview with Page Six, said he "completely disagree[s] with the narrative and happen[s] to think the world of Kimberly." However, other insiders claim that Guilfoyle hasn't integrated well into the Trump family, no matter how hard she tries. Prominent Trump family members like Melania, Ivanka, and Donald Trump have reportedly had issues with Guilfoyle, which could be causing tension between her and her fiance. In any family, it's challenging when a significant other doesn't fit in, and this is likely amplified within the famous and sometimes unpredictable Trump family.

5. Unusually long engagement period with no wedding in sight

CONROE, TX - OCTOBER 03:   Kimberly Guilfoyle and Donald Trump Jr. are seen at a Ted Cruz Rally at t
Kimberly Guilfoyle and Donald Trump Jr's have had an unusually long engagement period with no wedding in sight (Getty Images)

Donald Trump Jr proposed to Kimberly Guilfoyle in December 2020, but the news of their engagement only broke in January 2022. While a four-and-a-half-year engagement isn't excessively long, considering they started dating in 2018, it raises some concerns. They have now been engaged for longer than they dated before getting engaged, suggesting one or both of them might be hesitating in moving forward. The past few years have been busy for the Trump family, and they might be waiting for a pause in Donald Trump's legal issues to hold the wedding. Alternatively, given their history of keeping significant milestones private, they might already be married without having announced it yet.

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