Red Flags Kimberly Guilfoyle & Don Jr.'s Breakup Was Messier Than Let On

Bon voyage! The powers that be would love you to believe that, after being appointed ambassador to Greece, Kimberly Guilfoyle was ready to set sail to the southeastern European country without a care in the world and absolutely no ill will toward her former fiancé Donald Trump Jr. and his stunningly younger girlfriend, Bettina Anderson. "I am so proud of Kimberly," Don Jr. gushed on X, formerly known as Twitter, shortly after his famous father seemingly found a way to dispose of Guilfoyle as the Donberly relationship imploded for all the world to see. Quite the rise and fall in Trump land, indeed.

Alas, when it comes to everyone putting on a happy face and acting like this split was smooth sailing, it appears nothing could be further from the truth. On the contrary, the countless red flags flapping in the wind from here all the way to Greece suggest the breakup was way messier than anyone let on. We're talking a breakup cover-up of epic proportions.

We would be absolutely remiss not to discuss the overlapping of it all. As you may recall, all you-know-what broke loose in September 2024 when a then-engaged Donald Trump Jr. was caught packing on the PDA with Palm Beach model and party girl Bettina Anderson at a local bar and restaurant in the affluent South Florida town. "They were definitely on a date," one eyewitness told the Daily Mail. 

Perhaps even crazier was Kimberly Guilfoyle remaining eerily tight-lipped once the damaging photos came out. She isn't exactly known for being demure or mindful. (Never forget the disastrous 2020 RNC speech she practically howled her way through.) A source close to Guilfoyle told the Daily Mail she was "blindsided" by the photos. "Kimberly either didn't know about Bettina — or didn't want to know. Did she hear whispers that Don Jr. was fooling around with someone else? Probably." 

To make matters even messier, Bettina Anderson tried to soft-launch her romance with Donald Trump Jr. from the get-go. In serious passive-aggressive fashion, Anderson stoked the fires by dropping Instagram posts that subtly pointed to her relationship with the president's eldest son. In December 2024, she went as far as to post a picture of a bouquet of flowers along with a card to her Instagram Stories. "Many Have Said You're Aging Out But I Think You're Perfect. ... Happy Birthday!" the card read. The only saving grace was Anderson's long finger carefully covering the mysterious sender's name. Talk about pouring salt in Guilfoyle's freshly gaping wounds. We all see what you were doing here, Anderson. This is classic Vaguebooking 101.

For what it's worth, the president's camp has also reportedly been keeping a close eye on Anderson's antics. In fact, a source told Mediaite that Donald Trump downright "does not approve" of his son's relationship with Anderson. "Bettina's presence is seen as a liability rather than an asset," the insider said. Great. He can get in line behind Guilfoyle, we suppose. 

Don't get mad, get even. Kimberly Guilfoyle may be staying quiet, but rest assured, she's getting her kicks in where she can — namely, when it comes to her scandalous revenge style. Shortly after those cheater, cheater, pumpkin eater photos came to light, Guilfoyle took matters into her own hands by letting it all hang out via an entire wardrobe of attire that left very little to the imagination.

Amid the rampant cheating rumors, Guilfoyle and Donald Trump Jr. were still expected to meet their professional obligations and make their scheduled sojourn to the Balkans in September 2024. "Incredible trip to Belgrade, Serbia and Bucharest, Romania with @donaldjtrumpjr," Guilfoyle posted along with a series of photos of herself on the business trip, clothed in tight-fitting and low-cut dresses that practically screamed, "Eat your heart out, Donny boy." As the old saying goes, revenge is a dish best served cold. 

Diamonds are forever? Not quite. For all intents and purposes, Kimberly Guilfoyle has been a pro at saving face and making nice following her very high-profile called-off engagement to Donald Trump Jr. Still, it took some time for her to come around to the idea of taking off her sparkly five-carat emerald-cut engagement ring. In fact, she was seemingly still donning the rock in November 2024 while attending the America First Policy Institute gala at Mar-A-Lago. As evidenced in a throwback photo of the event Guilfoyle posted in February in celebration of both Robert F. Kennedy Jr. and Tulsi Gabbard's confirmations, she is seemingly sporting a large-and-in-charge ring on that finger! 

It should be noted, however, that Guilfoyle was later spotted sans the infamous engagement ring. Maybe she finally took the advice of the diamond pro who said she could make some serious cash selling Don Jr.'s engagement ring. The world may never know.