Painfully Obvious Signs Kimberly Guilfoyle & Don Jr.'s Marriage Would've Been Miserable

Ever since Kimberly Guilfoyle and Donald Trump Jr. split in late 2024, we've often wondered what could've been. Don Jr. confirmed the not-so-shocking breakup to Page Six, telling the outlet, "Kimberly and I will never stop caring for each other and will always keep a special bond." Referring to Guilfoyle's new gig in Greece, which will reportedly upend her 'Margarita Girl Lifestyle,' he added, "I could not be more proud of her and the important role she'll continue to play in my father's administration." Although President Donald Trump's son praised his ex-fiancée in his parting message, there are many signs that it would've been miserable for both if they'd made it down the aisle. 

One of the most painfully obvious signs was the rumor Guilfoyle was more interested in the Trump lifestyle than she was in love with Don Jr. "Let's just say that Don Jr. and the rest of [the family] got the [distinct] impression that Kimberly liked the idea of being a Trump more than she liked him," a source told Radar Online. And that could only have ended in fireworks (not the good kind) had they gone through with their marriage. But that's not the only glaring red flag that it would've been unholy matrimony.

Kimberly Guilfoyle and Donald Trump Jr. have a bigger age gap than we knew, and the almost nine years between them may have caused problems had they become husband and wife. Though plenty of political couples have massive age gaps and make it work, the ideal age gap, according to research published by the Journal of Population Economics, is up to three years. As ChoosingTherapy.com counselor Kristin Davin, LMHC, explained, having a large age difference can lead to friction caused by being in different phases of life, having different social or cultural experiences, or not having the same maturity level.

But it's not just between Guilfoyle and Don Jr. where her age could have made for awkward moments. The staunch Republican was born in 1969, which makes her one year older than her would-be step-mother-in-law Melania Trump — and that could've made for some odd power dynamics during family gatherings at the White House or Mar-a-Lago.

Though a couple having different fashion styles may not seem like a big deal, in a political family as big and famous as the Trumps, it could be seriously detrimental. According to People, Donald Trump Jr. was never a huge fan of his ex's clothing choices, which we can understand, seeing as Kimberly Guilfoyle has made some major fashion and beauty mistakes we begged her to ditch. "Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual," an insider claimed. "The tight dresses need to go and she has been told that."

They also claimed that Don Jr. felt Bettina Anderson, his first girlfriend post-Guilfoyle, had a lifestyle more fitting with the Trump aesthetic. "Don Jr. has always wanted to look good in his father's eyes. Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress him," they said. Had Guilfoyle and Don Jr. married, she may have felt pressure to change not only her fashion but her lifestyle to match what Don Jr. was looking for. As much as relationships can be about compromise, it would've been a red flag if the TV personality felt she couldn't be, or dress as, her authentic self around her fiancé.

Had Kimberly Guilfoyle become the latest Mrs. Trump, she may not have received a warm welcome from her new in-laws. Though Guilfoyle and President Donald Trump seem cordial in front of the cameras, a source told Politico in 2021 that he's no fan of the former Fox News star. In fact, Donald seemed to have the ick for Guilfoyle, particularly while she was working alongside former Governor of Missouri Eric Greitens amid his Senate bid. "Trump thinks Greitens is problematic, and that Kim is annoying," a source told the outlet, claiming Donald was upset about Guilfoyle working with Greitens.

There were other rumors about the Trump clan not approving of Guilfoyle. "Despite what the Trumps might say in public, they were never fully behind Kimberly. Some of them were even turned off by her, though they'll never admit it," a source told Radar Online. If they'd tied the knot, it was probably a ticking time bomb until a family feud erupted.

Donald Trump Jr. had no problem being photographed with Bettina Anderson while still engaged to Kimberly Guilfoyle, so chances are his wandering eye would still have come out even if they were married. A source told People that Guilfoyle supposedly knew about Don Jr. and Anderson's relationship before they officially split. "For the most part Kim has looked the other way because she loves the power and lifestyle," they claimed, purporting Don Jr. let people know he was with Anderson while still engaged. "[He] introduced [Anderson] around as his girlfriend when he was still very much with Kim," they said.

As awkward as Don Jr.'s new romance may have been for Guilfoyle, it would have been worse had he found a new love during their marriage. With extra years added to their romance and legal documents tying them together, a divorce would have been far tougher to handle than a broken engagement, and seeing her husband with another woman would likely have stung even more. So, it's safe to say a Guilfoyle and Don Jr. marriage would have been pretty darn miserable for everyone.