The Major Warning Signs Kimberly Guilfoyle And Don Jr. Were Never Meant To Last

Kimberly Guilfoyle and Donald Trump Jr.'s relationship has fascinated the world for years. The political couple were first linked in May 2018, when Page Six reported they'd been dating for several weeks in the wake of his split with ex-wife Vanessa Trump. They got engaged two years later, but it hasn't exactly been butterflies and rainbows since then.

Infidelity rumors plagued their relationship, no more so than when Donald Trump Jr. was spotted getting cozy with socialite Bettina Anderson in August 2024. A source told Daily Mail they weren't hiding their romance either, claiming, "They were definitely on a date. They weren't exactly making out, but the kisses were romantic, and you could tell they were intimate with each other." The strangest thing here? Guilfoyle never spoke publicly about her fiancé's dalliance with another woman. "For the most part Kim has looked the other way because she loves the power and lifestyle," a source told People in December 2024, the same month Don Jr. and Anderson were snapped together again.

Though Guilfoyle, one of our worst dressed celebs of 2024, and Don Jr. didn't explicitly confirm they'd split, he hinted their fractured fairytale was over to Page Six that month. "Kimberly and I will never stop caring for each other and will always keep a special bond," he said. But Don Jr. stepping out with Anderson was hardly the only warning sign his and Guilfoyle's relationship was never meant to last.

In public, Kimberly Guilfoyle seemed to have a good relationship with Donald Trump Jr.'s famous family. "I think I have a very good relationship with the president. I think I enjoy a very straightforward and authentic, very genuine relationship," she told The Mercury News in 2017, confirming she knew Donald Trump years before dating his son. However, rumors swirled things weren't so cordial behind the scenes.

When Guilfoyle and Don Jr. started dating, the media ate up their relationship — which reportedly irked Trump's sister. The Atlantic claimed Guilfoyle upstaged Ivanka Trump and Jared Kushner, who have a few relationship red flags of their own, when she attended her first family Fourth of July party. That went down so badly she wasn't invited to their Thanksgiving celebration that year. A source also claimed Donald turned down Guilfoyle for a White House press secretary gig. Then there was Ivanka's notorious Instagram upload cropping Guilfoyle out of Tiffany Trump's 2022 wedding and Radar Online's source claiming in 2024, "Despite what the Trumps might say in public, they were never fully behind Kimberly. Some of them were even turned off by her." With the Trumps so tight knit, it's unlikely a partner will last long without the family's full support.

Donald seemed happier to give Guilfoyle a political position following her split with his son, though — one that would send her to another country. In December 2024, Donald announced Guilfoyle was nominated as U.S. ambassador to Greece. But a source told People Don Jr. and his new love may have been behind the decision. "Bettina [Anderson] wants Kim out of the area. They are trying to send Kim abroad," they claimed.

A little disagreement here and there with your partner can be normal, but if you're regularly falling out in public and don't care who sees, that could be a bad sign. One source told Page Six in December 2024 that Donald Trump Jr. and Kimberly Guilfoyle's relationship had been contentious for a while, which is never a good sign for a relationship's longevity. "Don and Kimberly haven't been getting along over the past year. They get argumentative at Mar-a-Lago in front of people. Nothing crazy, but you know when a couple is fighting. They bicker in public," they said. Though it's not clear what the couple butted heads over, a source told Radar Online the month prior, "Let's just say that Don Jr. and the rest of them got the distant impression that Kimberly liked the idea of being a Trump more than she liked him."

Equally, in October 2024, a body language expert revealed Guilfoyle's dead giveaway for a troubled romance with Don Jr. "Her legs are crossed away from his so that's not where her energy is going. It seems small but it's a big deal," Traci Brown, CSP, told Nicki Swift, analyzing a clip of the then-couple chatting with Eric Moutsos posted to Instagram. 

As Kimberly Guilfoyle and Donald Trump Jr.'s romance hit the headlines, so did her alleged troubling behavior at Fox News. The TV personality left the network in July 2018 and HuffPost and The New Yorker alleged she'd departed because sexual misconduct allegations were made against her. She strongly denied that. "In my 30-year career working for the SF District Attorney's Office, the LA District Attorney's Office, in media and in politics, I have never engaged in any workplace misconduct of any kind. During my career, I have served as a mentor to countless women, with many of whom I remain exceptionally close to this day," she said in a statement.

Of course, dating anyone who's been accused of sexual misconduct should be done with a lot of forethought and an open dialogue with the person accused. But what was most telling is that Don Jr. never publicly supported his girlfriend with his own statement, despite her professing her innocence. That could be a warning sign he was more interested in protecting his own reputation and was too weary of the potential backlash publicly supporting his love could cause.

Notably, the businessman was happy to publicly defend his love from a more frivolous New York Daily News article in June 2018. It read of Guilfoyle, "When it comes to picking men, though, she'd be better off picking grapes." And Don Jr. wasn't happy. "How did this get past her editors at the @NYDailyNews? Or do they condone this kind of talk? I guess hypocrisy, sexism & racist rhetoric are alive & well there," he wrote on X, formerly known as Twitter.

There's nothing wrong with a long engagement, as many couples use the time after popping the question to plan their big day and gather funds. But we feel there was more behind Kimberly Guilfoyle and Donald Trump Jr.'s lengthy betrothal. He proposed on New Year's Eve 2020, but still wasn't married to Guilfoyle when he was spotted with Bettina Anderson nearly four years later in 2024. That put the duo well outside the 12-to-18-month average Brides reported U.S. couples take to go from engaged to married. The two likely had access to the best party planners and wedding venues in the world (Don Jr.'s dad Donald Trump is known to throw lavish affairs at his Mar-a-Lago estate), and we doubt they needed to save up for their dream day. According to Celebrity Net Worth, Guilfoyle has amassed $25 million, while her now former husband-to-be is worth a massive $350 million.

Making their lack of haste to walk down the aisle odder was how excited Guilfoyle seemingly was to marry Don Jr. in 2021. "Being his wife would be something that ... I think would be fantastic. I absolutely adore the family," she said on "Successful Philanthropy" (via Page Six). "I already feel married to him," she added. Only, legally, it seems she never will be.

Shortly before he began his relationship with Kimberly Guilfoyle, Donald Trump Jr. was married to Vanessa Trump, the mother of his five children, for 12 years. She filed for divorce in March 2018 and, just two months later, Trump went public with the former Fox News host. "Don Jr. and Kimberly are seeing each other, and are having a great time. While he wants to respect the privacy of his family, he is getting divorced, and he enjoys Kimberly's company," a source told Page Six. Don Jr. and Vanessa didn't finalize their divorce until February 2019.

Don Jr. and Vanessa ending a relationship that didn't serve them isn't necessarily a warning sign things weren't going to work out with Guilfoyle. However, jumping quickly from one relationship to another, especially one so lengthy and serious, does give us pause. There's no specific timeline for moving on, as every relationship and person is different, but MentalHealth.com recommends waiting one month for each year of the relationship to truly heal before getting back out there.