Don Jr & Kimberly Guilfoyle Moments That Predicted Their Split

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Kimberly Guilfoyle has had quite the rise and fall in Trump land. Since she first started dating Donald Trump Jr. in 2018, the former Fox News personality has worked hard to make a name for herself within the MAGA movement. Indeed, she became one of Donald Trump's most ardent supporters and was a staple of both the 2020 and 2024 election campaigns. However, all that time in the spotlight also made her a target of never-ending speculation –- especially when it came to her love life.

Guilfoyle's relationship with Don Jr. was a favorite talking point for years, as rumors of troubles in paradise and an eventual separation ran rampant. In November 2024, the couple's last-ditch attempts to squash split rumors backfired, and stories that they had called off their engagement reached a peak following election night. While both Don Jr. and Guilfoyle initially refused to speak on the matter, his apparent flirtations paired with her scandalous revenge style sure didn't help squash the chatter. Ultimately, Don Jr. confirmed what we all knew in mid-December 2024, telling Page Six he wanted nothing but the best for his ex. Here are all the red flag moments that predicted the couple's split long before it became official.

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Donald Trump Jr. didn't waste time moving on from his wife of 12 years, Vanessa Trump, after she filed for divorce in March 2018. Just two months later, Page Six confirmed that Don Jr. had started dating Fox News host Kimberly Guilfoyle several weeks earlier, despite the fact that his divorce wasn't even finalized yet.

In the months that followed, Guilfoyle made headlines when Fox News suddenly fired her from "The Five." It would later be revealed that the network actually paid $4 million to settle a lawsuit brought forth by Guilfoyle's former assistant accusing her of sexual harassment. Even so, that didn't stop Don Jr.'s new flame from becoming a central figure in Donald Trump's 2020 re-election campaign.

In addition to being named finance chair, she repeatedly popped up at rallies across the country. She became such a staple that during a joint appearance on The View with Don Jr., the couple was asked when they planned to marry, given their obvious shared interests. As they began to awkwardly talk over each, Guilfoyle explained that they were a team and already lived together. As for Don Jr., he made it clear they were focused on his dad's re-election and not their own love story. "We got one goal for 2020," he said, bypassing all talk of romance and even making a joke at his girlfriend's expense. "My big sacrifice for America is having to travel with Kimberly," he quipped.

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Following Donald Trump's political loss in November 2020, it seems Don Jr. was finally willing to shift focus to his love life. That New Year's Eve (which also happens to be his birthday), he finally proposed to Kimberly Guilfoyle –- who accepted. Jump to February 2021, and the newly engaged Guilfoyle told "Successful Philanthropy" (via Page Six), "I already feel married and committed to him, 100%." Noting that they'd known each other for 14 years, she shared that she loved her fiancé's humor and gushed about making the perfect team.

Even so, her dream partner didn't seem in a hurry to walk down the aisle. Nearly three years later, they were still engaged, and it seems some folks forgot the engagement even happened. During a cringeworthy appearance on Newsmax in September 2023, Guilfoyle was asked about Donald Trump by host Greg Kelly who dubbed him her "potential father-in-law." Well, that clearly hit a sore spot with Guilfoyle who instantly clapped back. "Potential?" she fumed. "Future father-in-law –- Jesus."

Despite Kelly's best efforts to turn things around, Guilfoyle refused to cut him any slack and continued railing against him, while also conveniently cutting a year off her engagement. "We've been engaged babe for two years, but we'll take this breaking news alert," she slammed. "That's hysterical."

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Donald Trump Jr. sent breakup rumors into overdrive in September 2024 after photos surfaced of Trump having brunch with Palm Beach, Florida socialite and model Bettina Anderson at a local hot spot called The Honor Bar. While the images simply showed them sharing a meal, multiple sources told the Daily Mail that the couple was clearly on a date. "They weren't exactly making out, but the kisses were romantic," one insider claimed, noting, "You could tell they were intimate with each other."

The headline-making encounter came just four months after Trump celebrated his six-year anniversary with Kimberly Guilfoyle. The two were seemingly still engaged, and a source told the Daily Mail just days after the original article published that Guilfoyle was blindsided by the photos. "Kimberly either didn't know about Bettina –- or didn't want to know," the insider mused, claiming that Trump's budding romance was an open secret in Palm Beach and alleging that Guilfoyle likely knew all about the rumors.

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Despite all the reports that Donald Trump Jr. had found love with another woman –- Bettina Anderson –- he and Kimberly Guilfoyle continued to put on a united front as they supported Donald Trump's 2024 run for president. Just a month after the Daily Mail published photos of Don Jr. dining with the socialite, he and his fiancé took a trip to Utah to try to win over Latter-day Saints voters.

The couple spent the weekend at Utah House Speaker Mike Schultz's ranch, posed for photos, met supporters, and even took time to sit down for an interview with podcaster and LDS member Eric Moutsos. While the conversation focused on politics, and the pair shared a similar message, their body language sparked new rumors about their relationship status.

As a body language expert told us, Guilfoyle's dead giveaway that there was trouble in paradise was the way she sat. "The first thing I noticed is that her legs are crossed away from his so that's not where her energy is going," Fraud-Busting Body Language Expert Traci Brown, CSP, told Nicki Swift. "It seems small but it's a big deal." Similarly, Don Jr. moved as close as possible to Moutsos and turned in his direction so much, their knees were practically touching.

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After months of speculation about their relationship status, Donald Trump Jr. and Kimberly Guilfoyle's behavior on election night confirmed what we suspected. As Donald Trump took to the stage to deliver his victory speech in November 2024, he was accompanied by his family, and the way his eldest son interacted with his fiancé, he did their romance no favors.

In a video posted to X, formerly known as Twitter, Guilfoyle can be seen pushing past several people behind Don Jr., then trying to push her way to be closer to him. Once they finally walked across the stage to take their spots, they did stand together, but had absolutely no interaction. Don Jr. turned sideways to watch his father speak, keeping his back to Guilfoyle the entire time, not touching her, and not even exchanging a single glance with his supposed bride-to-be.

Sparking even more chatter was the fact that Guilfoyle was visibly missing from an election night photo that featured Don Jr. and most members of the Trump Family. Don Jr.'s daughter, Kai Trump shared the snap to X, which also featured her mom and Don Jr.'s ex-wife, Vanessa Trump.

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If Donald Trump Jr. wanted to brush aside rumors of a new fling with Bettina Anderson, the tabloids made that real difficult in December 2024, as photos were released of the pair holding hands while walking at night in Palm Beach, Florida. The duo was reportedly leaving Anderson's birthday dinner, which took place at a luxe eatery called Buccan. Earlier in the day, Trump sent his new love flowers alongside a cheeky birthday card Anderson posted on her Instagram Story (via Daily Beast) that read, "Many have said you're aging out but I think you're perfect."

Further fanning speculation of a breakup with Kimberly Guilfoyle, Don Jr. was repeatedly spotted coming and going from Anderson's townhouse, which is conveniently located just 1 mile from Mar-a-Lago. The snaps were published just weeks after another insider told Page Six the couple wasn't in a good place and that the drama between them had started long before Anderson. "Don and Kimberly haven't been getting along over the past year," they alleged. "They get argumentative at Mar-a-Lago in front of people."

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Kimberly Guilfoyle's engagement all but fell apart in the public's opinion in December 2024 when she was offered a job in a faraway country. It was only hours after photos were published of Donald Trump Jr. holding hands with Bettina Anderson that Donald Trump took to Truth Social to announce he'd appointed Guilfoyle as the United States Ambassador to Greece. "Her extensive experience and leadership in law, media, and politics along with her sharp intellect make her supremely qualified," he praised.

However, many thought the president-elect had ulterior motives. While Guilfoyle proudly accepted the assignment, and Don Jr. praised her on X, critics were quick to point out that the job was a great way to keep her happy while also physically distancing her from Don Jr. That's because, if confirmed, the former Fox News host would have to move to Athens for the duration of her tenure.

Indeed, one source told NewsNation, "It's a consolation prize." As for why the couple hadn't publicly announced their split yet, the insider teased that it was imminent. Indeed, Page Six confirmed the same day as Donald's appointment that the duo had called it quits, although Don Jr. didn't confirm the speculation until a few days later, telling Page Six, "Kimberly and I will never stop caring for each other and will always keep a special bond."