Red Flags In Kimberly Guilfoyle And Don Jr.'s Relationship We Just Can't Ignore

One of the most captivating aspects of watching Donald Trump's family come together for his 2024 campaign was the unique dynamics of the various Trump family couples. For example, Eric Trump and Lara Trump emerged as a united front at the center of the action, while Ivanka Trump and Jared Kushner stayed firmly on the sidelines to focus on their children. Although these relationships seemed relatively straightforward, one pairing remained distractingly mystifying throughout the election season: Kimberly Guilfoyle and Donald Trump Jr. 

Engaged since New Year's Eve 2020, the couple once appeared destined for the alter. Guilfoyle has been spotted wearing a massive engagement ring on multiple occasions, and the two were still all smiles in many of their public appearances for several years. However, as the 2024 campaign season wore on, red flags emerged in their relationship that we just can't ignore. Here, we'll break down all the glaring issues we've seen in this not-so-storybook romance. 

Jumping from one relationship to another isn't usually a great idea, and the timing of Donald Trump Jr. and Kimberly Guilfoyle beginning their romance suggests that she may have initially been just a rebound for the eldest Trump son. Trump Jr.'s first wife, Vanessa Trump, filed for divorce in March of 2018 after years of marital strife, and Don Jr. barely let the ink dry on the divorce papers before moving on with Guilfoyle. 

In early May of that same year, a source told Page Six that the twosome had already been an item for a few weeks. The pair were reportedly seen attending a party together, perfectly happy to advertise their budding romance despite Don Jr.'s status as a still (technically) married man. Trump Jr.'s failure to take any time to reflect and recover from the demise of his marriage is a huge red flag, and it's the polar opposite of Guilfoyle's situation at the time. After all, Guilfoyle's relationship with ex-husband Eric Villency ended in divorce in 2009, giving the former Fox News correspondent plenty of time to emotionally heal and ready herself for another serious relationship. 

Although Donald Trump Jr. gave Kimberly Guilfoyle an engagement ring in 2020, the pair chose to hide their happy news for two whole years. Keeping such a big secret for so long was a strange choice for a couple that is so willing to be in the public eye, but it isn't even the most eyebrow-raising detail about their engagement. Despite announcing this relationship milestone in 2022, the couple seemingly made no further steps toward wedding bells. 

While taking time to enjoy being engaged is common, most couples still begin making plans, such as setting a wedding date. However, Guilfoyle and Trump Jr. made no such announcement, and their fiance status went virtually unaddressed throughout Donald Trump Sr.'s presidential campaign. It's possible the pair were waiting until after the election to take this huge step, but the other issues in their relationship suggest that getting married may not be a priority anymore. 

Public displays of affection can be awkward to watch from even the most tight-knit couples, but Kimberly Guilfoyle and Donald Trump Jr.'s PDA gave us second-hand embarrassment multiple times over the years. For example, back in March 2023, long before the issues between these two became impossible to ignore, audiences got a subtle hint that Trump Jr. wasn't quite so smitten with Guilfoyle at the 2023 CPAC. 

The two held hands in a sign of solidarity, but they looked anything but united. Their body positioning was truly bizarre, with Trump Jr. seemingly doing everything he could to maintain physical distance from Guilfoyle. Their facial expressions were also unbearably awkward — we're still cringing just thinking about it. 

Unfortunately, their PDA has only become more puzzling since that very public moment. For example, Guilfoyle shared an Instagram post in which she and Trump Jr. share a very fake-looking peck on the cheek. The two look more like acquaintances than an engaged couple, adding fuel to the rumor fire about an impending split. 

Although some couples prefer to keep their romance off of social media, Kimberly Guilfoyle and Donald Trump Jr. seemed perfectly comfortable broadcasting their relationship to their followers. Once upon a time, Guilfoyle frequently shared photos of them with touching captions that suggested a happy, harmonious union. For example, in April 2024, she captioned an Instagram post: "In each other's corner, taking on life together head-on with determination and dedication." This certainly feels warm and cozy and aligns with the sentiments she shared about Trump Jr. in the past. 

However, those lovey-dovey posts have become less and less common over time. By August 2024, Trump Jr. had all but disappeared from Guilfoyle's posts, and the few times he could be spotted amongst campaign-related content were far less personal than in previous years. In an October 2024 Instagram post, the pair stand shoulder to shoulder but aren't even holding hands — a far cry from the side hugs of yesteryear. 

This change is a huge red flag in itself, but the situation appears even more dire on Trump Jr.'s Instagram profile: aside from an April photo commemorating their sixth anniversary, you would barely know Kimberly Guilfoyle even exists from looking at his 2024 posts. Though they continued to appear together in public throughout Donald Trump Sr.'s 2024 presidential campaign, their social media feeds make it clear that this longstanding couple was already drifting apart. 

Of all the signs of trouble in paradise we've seen between Kimberly Guilfoyle and Donald Trump Jr., none is more telling than the swirling infidelity rumors that have plagued the couple. Unfortunately for Guilfoyle, it appears these rumors have plenty of truth to them: in September 2024, a source told OK Magazine that Trump Jr. went on a date with another woman. According to the source, Trump Jr. enjoyed a night out in Palm Beach, Florida, with socialite Bettina Anderson, and the evening was definitely not platonic: "They weren't exactly making out, but the kisses were romantic, and you could tell they were intimate with each other." 

Although Guilfoyle tried to quell the affair rumors, it has become increasingly obvious that Trump Jr. is up to his old tricks again. In 2018, sources told Page Six that the entrepreneur cheated on ex-wife Vanessa Trump with singer Aubrey O'Day back in 2011 and reportedly told O'Day that his marriage was already falling apart. It's hard not to wonder if Trump Jr. sold Anderson a similar story about his connection with Guilfoyle during their Palm Beach date.