The Biggest Rumors About Kimberly Guilfoyle

Kimberly Guilfoyle has had high profile jobs and relationships, which has put her in the public eye and led to rumors about her life both professionally and personally. Perhaps the most salacious of these reports was when Guilfoyle was forced out of Fox News. In July 2018, the network announced they were parting ways with the TV personality. Shortly afterwards, details began to trickle in about her dismissal. According to a report from the Huffington Post that was verified with multiple anonymous sources, Guilfoyle had been under investigation from Fox's human resources for sexual misconduct at the workplace. Reportedly, "The Five" host had shown photos of male genitalia to co-workers on multiple occasions, and had been abusive towards hair and makeup staffers.

More light was shone on Guilfoyle's sudden firing from Fox when The New Yorker published a report claiming that Fox paid $4 million to an assistant she had allegedly harassed, as the network wanted to keep the issue under wraps. That assistant started working for Fox straight out of college, and detailed how she was harassed by Guilfoyle. That included spending time at Guilfoyle's apartment where the on-air personality divulged graphic details about her sex life. The assistant claimed Guilfoyle would often be undressed in front of her, and ask the assistant for feedback on her physique. Guilfoyle released a statement to The New Yorker denying the allegations. "I have never engaged in any workplace misconduct of any kind," it read.

A year before the Fox News firing, Guilfoyle was implicated in a potential cheating controversy.

In the summer of 2017, Kimberly Guilfoyle was rumored to be dating Anthony Scaramucci. What made this reported romance so messy was that Scaramucci's divorce from his wife, Deidre Ball — who was nine months pregnant, was announced in July 2017. According to the Huffington Post, Scaramucci took exception with New York Magazine reporter Olivia Nuzzi, who reported in August 2017 that he was out for dinner with Donald Trump and Melania Trump, and that Guilfoyle joined them. Amid his divorce, Scaramucci did not want people gossiping about him and Guilfoyle. Gossip is exactly what followed, as it was reported by Showbiz411 that the then-Fox News host was apartment hunting with Scaramucci. That turned out to be a half-truth, as Scaramucci was looking at a unit in Guilfoyle's building and had asked for her input. "Just to get her thoughts," a source explained to People in August 2017.

Later that year, the two were spending time together, but there was nothing official about their relationship status. "It is too early to call them a couple," a source told Page Six in October 2017. "Kimberly thinks the world of Anthony ... He is still going through a divorce," the insider added.

The following month, Scaramucci returned to his wife and the couple called off their pending divorce in November 2017. Meanwhile, Guilfoyle was romantically linked to a younger bartender at the time, per the New York Daily News. Guilfoyle became the subject of more gossip as people believed she went to extreme lengths to look younger herself.

Many fans believe Kimberly Guilfoyle has undergone a litany of plastic surgery procedures, and she drew the ire of those fans when she attacked Nancy Pelosi's appearance in October 2022. Appearing on Newsmax, the TV personality had unkind words for the politician. "Pelosi lying, what's left of her face," Guilfoyle said (via the Daily Mail). "It's a freak show," she added. Multiple X, formerly Twitter, users accused Guilfoyle of hypocrisy. "It's hilarious how Kimberly Guilfoyle is attacking Nancy Pelosi on her use of Plastic Surgery when she herself had so many operations done," one X user commented at the time. "Kimberly Guilfoyle was talking about Nancy Pelosi's plastic surgery but she must have forgotten about these photos," another added while including an older snap of Guilfoyle and a more recent photo for comparison.

A year after receiving backlash for her Pelosi comments, Guilfoyle was once again accused of undergoing major cosmetic procedures. In October 2023, Guilfoyle shared a video to promote "The Kimberly Guilfoyle Show" on X. Several X users popped up in the replies to bash her appearance. "I don't know what doctor did your plastic surgery, but you should sue them," one wrote. Just two months later, Guilfoyle posed for a spread in Impact Wealth Magazine. Once again, detractors focused on her appearance. "What stands out more is the amount of fillers, botox, and plastic surgery on her face," an X user wrote.

Some of the harsh criticism stems from Guilfoyle aligning herself with the Trump family.

Kimberly Guilfoyle had known Donald Trump Jr. for years before they were romantically involved, as the pair had ties dating back to the late 2000s. Rumors of possible infidelity started to spread when news was made public that they were together. Donald Jr. had just announced he was divorcing Vanessa Trump a couple months earlier, so some suspected overlap in the relationships. "Don Jr. and Kimberly are seeing each other, and are having a great time," a source told Page Six in May 2018. "While he wants to respect the privacy of his family, he is getting divorced," they added.

The following month, Vanessa came to the defense of her ex-husband's girlfriend. "The lengths people will go to attack a woman simply because she's dating Don," Vanessa wrote on X in June 2018 while quote-tweeting a report about the New York Daily News saying that Guilfoyle was unfit to comment on politics while dating Donald Jr. due to a conflict of interest. Vanessa also clarified the timeline of their breakup, and made it clear that Donald Jr. started dating Guilfoyle after their split. "We've been separated for over 9 months and respect each other's decisions & privacy," she added. Days later, Guilfoyle made their relationship Instagram official when she posted a snap of herself, Junior, and Bret Michaels of Poison fame.

While their relationship timeline was above-board, reportedly not everyone in the Trump clan supported the union.

People started to speculate over how Donald Trump Jr.'s siblings felt about Kimberly Guilfoyle after she was mercilessly cropped out of a family photo at Tiffany Trump's wedding in November 2022. Ivanka Trump posted a photo to Instagram with the Trump ladies posing in bright pastel dresses, while Guilfoyle — who wore black — was edited out. This led many to believe there was friction between the former Fox News reporter and her fiance's family. 

Shortly after the wedding photo debacle, Page Six spoke to a source that said the Trumps were not too keen on Donald Jr.'s partner. "The vibe is that the family doesn't like Kim. She is trying too hard to be in the family," the insider told the outlet in December 2022. One sibling, however, came to the defense of Guilfoyle. "I completely disagree with the narrative and happen to think the world of Kimberly," Eric Trump told Page Six when asked for comment.

That was not the end of the rumors, as OK! reported in February 2023 that the feud between Ivanka and Guilfoyle was still heated. "Ivanka doesn't trust her because she sees her as a social climber desperate to marry into the family," a source told the publication. Per the insider, the crop-job from the wedding pic was no mistake. "Kimberly knew the dress code and simply disregarded it, which upset both Tiffany and Ivanka," they added. Donald Jr.'s siblings were likely not thrilled to hear reports about his wedding plans with Guilfoyle. 

Initially, reports of Kimberly Guilfoyle's engagement to Donald Trump Jr. left many wondering if the couple were actually engaged. Questions arose, as the pair had a non-traditional rollout to announce their pending nuptials. In January 2022, the Daily Mail reported that the two were engaged. The surprising part of the news was how long they hid the news from the public. "They've kept it private for the past year as they settled into life in Florida after moving from New York," a source told the outlet. "It's been an open secret for the past 12 months with everyone Kim runs into admiring her almost 8 carat diamond engagement ring," the insider added. A different source confirmed to People a few days later that Donald Jr. had indeed popped the question, but there was no confirmation from the couple themselves.

Over a month later, the engagement graduated from rumored to confirmed when Guilfoyle gushed over her fiance on Instagram. She uploaded a carousel of photos of the couple and included a touching caption. "Falling in love with my fiance [ring emoji] more and more every day ... @donaldjtrumpjr, you're my best friend, my support system and my forever guy," she wrote. Even though they had been engaged for over a year, the couple had still not announced a wedding date.