5 Signs Kimberly Guilfoyle & Don Jr.'s Breakup Was Messier Than It Seems

The numerous red flags in Donald Trump Jr. and Kimberly Guilfoyle's relationship have become increasingly hard to ignore in recent weeks, and now we know why. Though the celebrity couple hasn't officially announced the end of their four-year engagement, photos showing the president's son getting cozy with socialite and model Bettina Anderson were proof enough. An unnamed source dished to People that the affair has been going on for six months but "For the most part Kim has looked the other way because she loves the power and lifestyle" of being in the Trumps' inner circle. 

Both she and Don Jr. reportedly wanted to keep the truth strictly under wraps until after the election, and with that deadline safely passed, things are now moving pretty quickly. The president-elect himself, Donald Trump, broke up with Guilfoyle in favor of Don Jr. by naming her the new U.S. ambassador to Greece earlier this week. And, although Don Jr. and Guilfoyle haven't done anything to suggest this is anything but a civilized conscious uncoupling, there are hints that things aren't quite so rosy behind the scenes. We did some detective work; see if you agree with our conclusions.

Wedding and engagement rings are such a traditional symbol of a couple's commitment that their sudden absence is usually a telltale sign that there's trouble afoot. How many times have you seen a gossip headline reading something like: "X Celebrity Spotted Without Wedding Ring?" Kimberly Guilfoyle, however, has continued to proudly sport her diamond ring in public as recently as this past Election Day (seen above). The huge 5-carat sparkler also became a subject of speculation when Guilfoyle and Donald Trump Jr. first announced their engagement. Although they came out as affianced on New Year's Eve 2021 — which is also Don Jr.'s birthday, FYI — sources clarified to the Daily Mail that the businessman had actually proposed a year earlier, right before then-President Donald Trump (reluctantly) turned the White House keys over to Joe Biden. 

Not until the happy couple had established themselves and their combined children in their new Florida digs did Guilfoyle start flaunting her bling. Now the wedding is apparently off, but the ring remains on. Is the former Fox News host trying to maintain a façade of romantic bliss until Don Jr. is ready to make an official announcement? Or is this a defiant message to her fiancé that she's not going to give him up without a fight? Either way, you can be sure that every paparazzo's camera lens will be trained on her left hand until Guilfoyle is ready to put the ring back in its velvet box for good.

If a picture tells a thousand words, an Instagram post tells a million. Social media offers us plebians a glimpse into the lives and thoughts of public figures, and the things they don't share can be just as significant as those they do. A peek at the IG feeds of both Donald Trump Jr. and Kimberly Guilfoyle is indeed revealing. The attorney-turned-media personality is quick to add likes to her man's posts — as if to plead, "I'm still in the picture!" — but Don Jr. notably hasn't done the same for hers in quite some time. He did congratulate Guilfoyle on her new ambassadorship, but offered no expressions of love or even mentions of spending the future by her side. Perhaps in retaliation, Guilfoyle took a sly dig at Don Jr. as she posted a victory lap of the praise she'd received from friends. 

In most cases, the former Fox News host included a photo of herself with the person giving her the shout-out, but tellingly didn't add a happy-couple pic when she shared her fiancé's message. Adding more intrigue to the mix, Guilfoyle follows Bettina Anderson, suggesting she might have been doing a bit of snooping for evidence of an affair. The socialite, on the other hand, doesn't appear to be one of Guilfoyle's followers. Several major events are on the horizon — Christmas, New Year's Eve/Junior's birthday, and Donald Trump's inauguration — and the images Guilfoyle and Don Jr. share or, more accurately, choose not to share should offer more hints about the civility (or lack thereof) of their breakup.

No relationship is perfect. Even the happiest of couples disagree at times — and sometimes those fights are heated. But when they leave closed doors, it can be a sign that the parties in question no longer care who knows about their problems. This seems to be the case with Donald Trump Jr. and Kimberly Guilfoyle. Page Six spoke to a source who confirmed that the couple has been airing their grievances within public earshot more often lately. "Don and Kimberly haven't been getting along over the past year," the insider disclosed. "They get argumentative at Mar-a-Lago in front of people. Nothing crazy, but you know when a couple is fighting. They bicker in public." 

That isn't that surprising, considering both parties' bold personalities and outspoken natures. The former Fox News personality, for instance, is well known for her often abrasive delivery. Guilfoyle's awkward speeches typically consist of her yelling about making America great again, and even shushing people who insist on chattering away in the background. Anyone who's willing to interrupt their own speech to scold a complete stranger for not paying attention is capable of snapping at her fiancé during a fancy dinner or a campaign fundraiser. And she would be especially likely to do so if that fiancé was caught sneaking around with another woman. 

Shortly after the breakup news went viral, Us Weekly jumped into the fray with a different take altogether. Far from being a devastating scandal, sources clarified that the whole situation had been going on for ages and that everything was just fine. Donald Trump Jr. and Kimberly Guilfoyle apparently parted ways on great terms back in late summer 2024 because of their "different goals," and they kept quiet so as not to take any attention away from Donald Trump's campaign. The outlet even claimed that Guilfoyle was starting to see other men, as if she had no problem simply letting go of a six-year-long relationship. 

Yet as of this writing, neither the former Fox News host nor Don Jr. has confirmed any of this publicly. If they really did break off their engagement in a civil manner, it would have been relatively easy to post an announcement on Instagram right after the Daily Mail bombshell dropped. You know the type: A plain background and a serious-looking font, with phrases such as "We have made the difficult decision" and "We ask that you respect our privacy at this time." The Us Weekly article comes off suspiciously like a frantic public relations effort to put a positive spin on a situation that's anything but amicable as a result.

The biggest clue about the nature of the couple's supposed split was the announcement of Kimberly Guilfoyle's ambassadorship. True, president-elect Donald Trump has been nominating wild cabinet positions nonstop since his victory, but he gave his would-be daughter-in-law a new job mere hours after his eldest son was caught with his purported new flame. That's just a little too conveniently timed to be a mere coincidence. Plus, there's the distance factor. Though Guilfoyle has no Greek heritage (she's Irish and Puerto Rican) and once even called Greeks "freeloaders," per The Independent, she'll nonetheless be 5,000 miles away from Florida and thus less likely to run into her ex and his new lady. 

In fact, a source told People that this was key to Trump's decision. "Bettina [Anderson] wants Kim out of the area," they posited. "They are trying to send Kim abroad." While the former Fox News host, and staunch Trump loyalist, may not be as thrilled about the appointment as she's claiming to be, the arrangement will allow Guilfoyle to heal from the breakup in a less public setting. Crucially, she'll also still be a part of Team Trump, though not as close to the presidential inner circle as the TV personality was before. Whether Anderson will occupy her former seat in the White House dining room remains to be seen.