Long before their breakup was made public, there were multiple moments that predicted that Kimberly Guilfoyle and Donald Trump Jr. would split. Their relationship came to a public end in December 2024 when photographs showed Trump holding hands with his new girlfriend, Bettina Anderson. Days later, the couple made it official that they had parted ways. "Kimberly and I will never stop caring for each other and will always keep a special bond," Junior told Page Six at the time. The pair did appear to be on amicable terms, and perhaps that was due to them ending their engagement behind closed doors much earlier. "Don Jr. has been dating Bettina for about six months," an insider told People after the snaps of Trump and Anderson were published. Apparently, Trump and Guilfoyle had an unspoken arrangement. "For the most part Kim has looked the other way because she loves the power and lifestyle," the source added.
Hindsight makes the signs that Guilfoyle and Trump's relationship wouldn't last much more evident. Take Trump's Instagram posts about Guilfoyle, for example. In March 2019, which was fairly early in their relationship, he made a gushing post for his then-girlfriend's birthday. "Thanks for everything you do and I look forward to celebrating many more of these with you," he wrote. Compare that to the birthday message Trump shared for Guilfoyle four years later. "Happy birthday to the best broad ever @kimberlyguilfoyle," he wrote in March 2023 while adding that it was an "inside joke" between them. There was an obvious disconnect, as that same year Guilfoyle made a heartfelt post for Trump's birthday. As their engagement came to an end, other Instagram posts tipped off followers that the two would not be tying the knot anytime soon.
Their neverending engagement gets called out
The way Kimberly Guilfoyle and Donald Trump Jr. announced their engagement was a giant red flag. In January 2022, the Daily Mail reported that the couple — who had been dating since 2018 — were engaged. That seemed to be a reason for celebration, but what made it odd was that Junior had popped the question a full year earlier on New Year's Eve 2020. At the same time their engagement became public, Guilfoyle showed off her ring for the first time in an Instagram post. "I can't wait to spend the rest of our lives together," she wrote in the caption of the post, which was also a birthday shoutout to her fiancé, whose birthday falls on New Year's Eve.
The following year, Guilfoyle had a minor on-air spat when the possibility of her actually tying the knot was called into question. Newsmax host Greg Kelly referred to Donald Trump Sr. as her "potential father-in-law" while interviewing Guilfoyle in September 2023, which clearly ruffled her feathers. "Potential? Future father-in-law. Jesus," she sternly retorted.
Near the tail end of their relationship, Guilfoyle and Don Jr.'s protracted engagement appeared to be an indicator that they were on the rocks. The couple both posted their own anniversary snaps to Instagram in April 2024 — which would have been a couple of months before they quietly called it quits. "Happy 6 year anniversary @kimberlyguilfoyle thanks for always being there no matter what the haters are throwing our way," Don Jr. wrote in his caption. For many followers, alarm bells were already ringing about the pair dragging their feet to the altar. "Are you guys going to finally get married?" one replied. "6 fkg years," another incredulously commented. Later, Don would be conspicuously absent from Guilfoyle's IG timeline.
Donald Trump Jr. goes MIA from Kimberly Guilfoyle's posts
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Donald Trump Jr. was a fixture on Kimberly Guilfoyle's Instagram page, but a red flag that their relationship had hit a rocky patch was evident once he started appearing less frequently. Up until the Republican National Convention in July 2024, Junior was featured in Guilfoyle's posts nearly once a week. For example, the Rumble media personality posted snaps of her and her fiancé's visit to El Salvador in late June 2024. A couple of weeks earlier, Guilfoyle had reshared a video showing the pair spending time with Russell Brand. By the time the RNC was over, Guilfoyle rarely posted selfies and began posting memes and posts centered on Donald Trump Sr.'s presidential campaign. "Is she still with Donald jr? He seemed distant to her," a follower commented on Guilfoyle's RNC post.
It's not as if Donnie completely vanished from Guilfoyle's Instagram timeline, but his appearances became sparser, and usually, the posts were from events. That August, Guilfoyle uploaded a carousel where the pair spoke at a fundraiser held at a Trump supporter's home. Raising funds and aligning herself with Donald Sr.'s campaign seemed to be Guilfoyle's primary concern.
The following month, a political expert said they believed Guilfoyle was waiting for the election to ultimately make a decision on the fate of her relationship with Don. "Basically, her career is closely tied to Donald Trump Jr.," journalist Tara Palmeri said on her "Somebody's Gotta Win" podcast in September 2024. "If Trump loses ... and this is all over, I can see her pivoting," Palmeri added. At the time, Palmeri was reacting to a bombshell revelation that had just emerged about Don and another woman.
The first photos with Bettina Anderson
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The most damaging evidence that Kimberly Guilfoyle and Donald Trump Jr. were headed for Splitsville was those photos of him with another woman. The Daily Mail published snaps in September 2024 that included shots of Trump dining with another woman — socialite/model Bettina Anderson. Those photographs were taken a month earlier and were accompanied by reports from eyewitness snoops. "She seemed totally smitten with Don – and he with her ... They were definitely on a date," one witness told the outlet. There was more evidence that this was more than just dinner between friends. "They weren't exactly making out, but the kisses were romantic, and you could tell they were intimate with each other," the source added.
A day after that scintillating report was published, the Daily Mail had more info about Guilfoyle and Trump's relationship. "Did she hear whispers that Don Jr. was fooling around with someone else? Probably," a Mar-a-Lago insider told the outlet. Apparently, it was not rare for Junior to do as he pleased. "He's pretty bold and, as smart as she is, Kimberly looked the other way," the source said.
Instead of keeping quiet on the matter, Trump's rumored new squeeze decided to respond with a thinly veiled Instagram post. Days after those reports surfaced, Anderson posted a three-pic carousel of herself posing in front of a "Private" sign. "Gossip is the devil's telephone," she wrote in the caption. Meanwhile, Guilfoyle fired back by sporting revenge-style revealing dresses. She also attempted to control the narrative by posting pics of her and Trump to prove their relationship was as strong as ever.
Kimberly Guilfoyle's desperate PDA pics
Kimberly Guilfoyle sprang into damage-control mode as soon as the reports of Donald Trump Jr. stepping out on her started circulating. Even though her fiancé had been mostly absent from her Instagram posts prior to the cheating rumors, Guilfoyle uploaded a PDA-packed Instagram carousel a day after the initial Bettina Anderson reports were published. Guilfoyle's post was a recap of her visit to the Patriots Day Freedom Fest in Kentucky alongside Trump. In a transparently mad dash attempt to prove the pair were still a couple, Guilfoyle included a pic of her and Junior embracing in front of the crowd. She also added a snap of her planting a smooch on his cheek for the audience. Not everyone was convinced by this overt display of affection. "Did Junior bring his girlfriend ... I mean the new one?" one follower commented on the post. Days later, Trump was right back on Guilfoyle's timeline when she posted photos from their dual appearance at the Texas Youth Summit.
The onslaught of fiancé-centric content continued for Guilfoyle on September 27, 2024, when she uploaded an Instagram carousel from their visit to the Balkans. There were multiple pics of the pair standing together, but they looked rigid and uncomfortable. The body language between the two was a giveaway that their relationship was doomed, as evidenced during a joint interview for Rumble Media in October 2024. The two kept their distance during the sit-down. "The first thing I noticed is that her legs are crossed away from his so that's not where her energy is going," body language expert Traci Brown told NickiSwift. That disastrous body language continued on election night when it became clear the couple would go their separate ways.
Donald Trump Jr. says goodbye to Kimberly Guilfoyle
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The behavior of Kimberly Guilfoyle and Donald Trump Jr. on election night seemed to confirm what many had suspected for months. It was a triumphant night for Donald Trump Sr. and the Trump clan, but Guilfoyle seemed to be slightly shunned. Video of the POTUS giving his victory speech showed awkwardness between Donnie and Guilfoyle in the background. Not only did he not stand close to his longtime partner, but Junior appeared to actively avoid standing next to Guilfoyle. To make matters worse for the former Fox News anchor, Kai Trump, who is one of Don's kids, threw some subtle shade at Guilfoyle. Kai posted a large group shot on X, formerly Twitter, the night of the election. "The whole squad," the teenager tweeted. Guilfoyle was noticeably absent from the shot, which even included Elon Musk and his son.
Later that month, a report surfaced that the reason Don Jr. and Guilfoyle seemed so distant was that the pair were just going through the motions. "It is all a show. The appearances of Don and Kimberly are for the cameras," a source told Radar in November 2024. "The Trump family does not want to create an enemy in Kimberly," they added.
The nail was officially put in the couple's relationship in early December 2024 when Donald Sr. announced that he was appointing Guilfoyle as the United States Ambassador to Greece. Junior, meanwhile, did not seem upset in the least to hear Guilfoyle was relocating overseas. "I am so proud of Kimberly. She loves America and she always has wanted to serve the country as an Ambassador," he wrote in a tweet that basically screamed "bon voyage" to his former fiancée.