All The Signs Kimberly Guilfoyle & Don Jr.'s Relationship Won't Last

At first glance, Kimberly Guilfoyle and Donald Trump Jr. appear to be a match made in MAGA heaven. However, you don't have to scratch too far beneath the surface to find signs that they very likely won't reach the romantic finishing line. In fact, it appears that the writing is already on the wall for the couple.

Don Jr.'s usually flashy fiancée has been uncharacteristically quiet since her rabble-rousing July 2024 Republican National Convention speech, further fueling the speculation that something is rotten in the state of #Donberly. Because let's face it: When Guilfoyle starts swerving social media, you know something just has to be wrong. There has been a distinct lack of love-struck PDA pics of Guilfoyle and Don Jr., and although she's been on serious damage control, quite frankly, at this point, Guilfoyle's desperate attempts to squash the Don Jr. split rumors are more embarrassing than convincing at this point.

As evidence mounts that love's middle-aged GOP dream is on the outs, it seems that no amount of cringey PDA moments between Guilfoyle and Don Jr. will save the sinking ship now. From getting cozy with a Palm Beach socialite to their never-ending engagement to Donald Trump and co's disapproval, we're examining the ever-increasing signs that Guilfoyle and Don Jr.'s relationship won't last.

Whenever Kimberly Guilfoyle busts out with a gushing declaration of love, Donald Trump Jr. looks totally checked out. Case in point: Guilfoyle's emotional speech during her 55th birthday celebration in March 2024. "I want to say thank you so much to my incredible fiancé, Donald Trump Jr.," she said as he cocked his head to the side, slouched over, hands in his pockets. "There is no man more supportive, that lifts me up every day, honors me, believes in me, and has literally been the greatest blessing in my life. He's really shown me what it's like to be loved and adored and blessed and protected and his loyalty and his fidelity and his enthusiasm for me is truly unparalleled."

At her birthday party, Kimberly Guilfoyle called Don Jr "the greatest blessing" in her life.

Guilfoyle: "His loyalty and his fidelity and his enthusiasm for me is truly unparalleled to what I've experienced in this life." pic.twitter.com/tP1riJf5we

— PatriotTakes 🇺🇸 (@patriottakes) March 12, 2024

Haters weren't buying Guilfoyle's narrative. They were eager to point out that Don Jr. allegedly cheated on his first wife, Vanessa Trump, so she shouldn't be shocked if history repeats itself — despite her claims of his undying devotion.

"Oh, honey ... you weren't the only person Don Jr. cheated on his wife with. So don't get too smug about his purported loyalty and fidelity," one wrote on X, formerly Twitter. "Oh I bet if someone a bit younger or just better looking wanted him they could have Don Jr.. Easy. Neither one is worth bragging over," another claimed. "No kiss after? After those caring words, he doesn't even go up to her," a third observed.

Donald Trump Jr. doesn't mind airing his Kimberly Guilfoyle dirty laundry in public. Not-so-doting Don Jr. expressed irritation at his feisty fiancée during a Q&A segment on his "Triggered" podcast in May 2024. "Kimberly for press secretary?" Don Jr. asked, repeating a viewer's question. "You know, that would be great. She can do like six days a week in Washington D.C. I get peace and quiet. Everyone wins," he decreed.

Just a joke about the "ball and chain," right? Hmmm. "I think it's a great idea. You know, she moves up to D.C., I get, like, four years of peace and quiet; like I said, everyone wins!" He repeated. And then: "Don Jr. sleeping on the couch tonight? Fact check true. But hey, listen, sometimes you sleep on the couch, and it's just worth it because it's just, it's just worth it," he mused.

"Kim's an animal," Don Jr. continued. "Like I said, I think she'd do a great job at the job. I get peace and quiet. Everyone wins!" he declared — again. "You think she's tough? You don't think I have to put up with that s***t?" Don Jr. concluded. "I do! That doesn't just turn off when you're not on a show or you're not on TV."

One clear sign that Kimberly Guilfoyle and Donald Trump Jr.'s relationship won't last is his cozy relationship with Bettina Anderson — something that Guilfoyle definitely won't be shouting about from the podium.

The Daily Mail obtained photos of Don Jr. brunching and munching with the 37-year-old Palm Beach socialite at Royal Poinciana Plaza's The Honor Bar on August 17, and the two definitely looked — friendly. According to an onlooker, Anderson kissed Don Jr. on the lips not once, but three times, in addition to rubbing his thigh. "She seemed totally smitten with Don — and he with her," the source said, concluding, "They were definitely on a date."

Donald Trump Jr. is 'caught kissing' glamorous Palm Beach socialite Bettina Anderson during brunch date without fiancée Kimberly Guilfoyle https://t.co/kkYXVwbacY pic.twitter.com/krhjmz19Lt

— Mail+ (@DailyMailUK) September 15, 2024

Meanwhile, another source told The Mail that Anderson and Don Jr. have been spotted together all over Palm Beach. Not surprisingly, social media was here for it, evoking the memory of his past behavior. "He cheated on his wife, the mother of his five kids, and his natural progression was to cheat on his mistress who became his fiancé who he still cheating on. Does it sound like someone else we know?" a commenter asked on X. "Kim and Don Jr. broke up a long time ago! I'm too lazy to bring up past posts but they've been done for over a year. Nobody notices because it's all crazy," another claimed. "Junior cheated on his wife ... with that thing he's with now. So why not. The apple ... yadayada," a third chimed in.

Kimberly Guilfoyle and Donald Trump Jr. started dating in April 2018, went Instagram official two months later, and got engaged on New Year's Eve 2020. The lovestruck couple marked their 2024 dating anniversary with his and her Instagram posts. "Happy 6 year anniversary @kimberlyguilfoyle thanks for always being there no matter what the haters are throwing our way. I love you," Don Jr. captioned a carousel of pics on April 25. Guilfoyle returned the sentiment with her own carousel and gushing declaration of adoration.

However, after nearly four years of engagement, there has still been no talk of a wedding — which is kind of weird for a couple who usually aren't backward about coming forward. Many believe that Don Jr.'s seeming reluctance to put a ring on it doesn't bode well for the future of #Donberly.

"He loves her so much he never proposes," a commenter noted on X. "They've been together for how many years now and he still hasn't married her," another observed. "Uh huh. How many years into their engagement is this? They must be so in love," a third sniped.

With her fiery and impassioned speeches, Kimberly Guilfoyle knows how to keep the MAGA crowd entertained. It's one of the reasons she's become an RNC favorite (and Democratic punchline). However, not everybody in the GOP is a fan. If rumors are to be believed, among those who would be happy to give Guilfoyle a swerve is her fiancé, Donald Trump Jr.'s family.

Reports of trouble in Trump-land paradise started after Ivanka Trump unceremoniously chopped her future sister-in-law out of a photo from Tiffany Trump's wedding that she posted on Instagram. "Where's Guilfoyle??" one commenter asked, adding a laughing emoji for good measure. "Congratulations for [removing] the witch out of the picture," another wrote, adding four laughing emojis for even better measure.

Despite Ivanka denying it was intentional and posting the unedited version on her Instagram Stories, many believed it was a sign that Guilfoyle was wearing thin on the Trumps. "The vibe is that the family doesn't like Kim," a source told Page Six in December 2022. "She is trying too hard to be in the family." Rift flames were fanned when Ivanka and Jared Kushner were MIA at Guilfoyle and Don Jr.'s Toys for Tots party at their flashy Palm Beach pad later that month. Meanwhile, Politico reported in July 2021 that Donald Trump was irritated by Guilfoyle's social climbing and that he believed she was using his family name to advance her political agenda.