How The Trumps Really Feel About Kimberly Guilfoyle

It's not always easy fitting in with future in-laws, and much has been made about contentious relationships between them over the years, both in real families and in Hollywood portrayals. Of course, fitting in with a former first family is likely even more difficult, and something former Fox News co-host Kimberly Guilfoyle is familiar with these days.

Guilfoyle has been engaged to Donald Trump, Jr., the eldest son of former President Donald Trump, since 2020 (news they managed to keep quiet for more than a year). When the pair eventually tie the knot, it will mark her third marriage overall, after previous unions with Democratic California Governor Gavin Newsom, which ended in divorce in 2006, and Eric Villency, whom she divorced in 2009. She has one child with Villency, a son, Ronan.

Guilfoyle has been a strong ally to her future father-in-law and even served as an advisor during his time in office. In her speech at the Republican National Convention in 2020, she spoke highly of Trump when campaigning for his presidency. "He [Trump] built the greatest economy the world has ever known ... President Trump is the law and order president," Guilfoyle said (via YouTube). But surprisingly, reports have swirled that the former Fox News commentator actually isn't well-liked by the Trump family at all. However, the former television host and political firebrand doesn't seem to be going anywhere, meaning that despite their feelings, those that don't like her might just need to grin and bear it. 

Kimberly Guilfoyle and Donald Trump, Jr. were first confirmed to be a couple in 2018 by his now ex-wife, Vanessa Trump — with whom he was immersed in a high-profile divorce at the time. However, Guilfoyle and Trump, Jr. had known each other for several years prior to that. Both he and Guilfoyle are known for their active presence on social media and seem like a good match because of their fiery personalities. It seems Donald Jr. also feels like he and his future wife are a good match.

Not only has he praised her on his Instagram account, where he referred to her as the "best broad ever" on her birthday in March 2023, but he has also spoken highly of her in the press, telling Moneycontrol in 2022: "It's true. [She has] just been an incredible partner for me, and again, that's not easy — a) I am difficult and b) the nonsense that you have to deal with just when you're in my world because the nature of what they've tried to do to my family, but more importantly also the nature of the way I then respond."

Guilfoyle has also gushed about her significant other, sharing in the December 2022 issue of Metropolitan Palm Beach magazine (via Insider) that she was super traditional in their relationship and made sure to always take care of him the way she saw her own mother do for her father.

Former President Donald Trump gave Kimberly Guilfoyle the role of an advisor for his presidency and even reportedly considered her as an option for his press secretary twice, before giving the positions each time to Sean Spicer and Sarah Huckabee Sanders. It turns out that Trump found Guilfoyle to be "annoying" and openly complained about decisions she made with her career while benefitting from her profile as an extension of the Trump family.

The biggest moment where Guilfoyle appeared to incur her future father-in-law's wrath came when she signed on as national campaign chair for Eric Greitens' 2021 campaign for the Missouri Senate. This decision infuriated Trump because he felt her association with him would be misconstrued as an implicit endorsement of the disgraced former governor.

Greitens became a disgraced figure in 2018 after he was charged with invasion of privacy for taking a nonconsensual photo of his hairstylist to blackmail her. Later, he was accused of assaulting his ex-wife, Sheena Greitens, and their children. "Trump thinks Greitens is problematic, and that Kim is annoying," an insider told Politico at the time. "He said, 'Why the f*** is she working for him?'" Politico also reported that Guilfoyle insisted via text message that "the notion that she and Trump are at odds is false." Whatever the relationship is between them, it's evident that her career choices have really irked the former president.

For many years, Melania Trump has been the subject of rumors that she doesn't like her own husband, especially following his arraignment in New York City. While the family has worked to deny those reports, they don't appear to be trying to refute claims that she doesn't trust a lot of the aides who have surrounded her husband over the years — including Kimberly Guilfoyle.

In an interview with MSNBC promoting her book, "I'll Take Your Questions Now: What I Saw at the Trump White House," Melania's former aide, Stephanie Grisham, revealed that the former First Lady is actually very protective of her husband and detests anyone who tries to profit off of him.

"She was always very protective of who was around her husband," Grisham said (via YouTube). "She very much liked people who would tell him the truth, tell him he shouldn't do things. ... She didn't like people profiting off of her husband or her family. And so, when you consider how much Jason Miller had made off of the Trump family, or I know Kimberly Guilfoyle demanded I believe $60,000 just to introduce the president the day of the rally, it was things like that, that bothered her. She just wanted people who had his best interests and the country's best interests at heart around him ... she never liked that kind of thing."

No one seemed closer to former President Donald Trump during his time in the White House than his daughter, Ivanka Trump, who served as his top advisor. But Trump's eldest daughter has made headlines for what is perceived as a public dislike for Kimberly Guilfoyle.

Ivanka notably hit the papers after she shared an image on social media of the Trump women at Tiffany Trump's wedding ... but Guilfoyle was cropped out of the photo even though she had been standing next to Ivanka in the original image (via Page Six). Ivanka later said she made a mistake and reposted the original image to her Instagram story afterward. "Once people online noticed, Ivanka reposted the image with Kimberly in it, but the damage was done," a source told OK! No explicit reason was given for the decision at the time, though rumors suggested that Ivanka disapproved of Guilfoyle's attire.

However, since then, it's been reported that Ivanka genuinely does not like her brother's fiancée at all and also doesn't believe she is someone who can be trusted within the family. "[Ivanka Trump] doesn't trust her because she sees her as a social climber desperate to marry into the family," a source told OK! in February 2023. Ivanka also reportedly preferred her former sister-in-law, Vanessa Trump, and believed there was "hope that they would reconcile" after her divorce from Donald Trump, Jr. but "Kimberly put the kibosh on that."

Jared Kushner has been a part of the Trump family since marrying Ivanka Trump in 2009, and like his wife, served as a close advisor to Donald Trump during his presidency. However, while he played a big role there and likely interacted with Kimberly Guilfoyle at times because of their mutual roles in the administration, it's not immediately clear where he lands when it comes to liking or disliking his future sister-in-law.

However, one thing that does seem to be clear about his relationship with her is that if his wife wants to set boundaries, he appears to support them, specifically when it comes to their lack of attendance at events Guilfoyle is present at or hosting. The pair are often absent from events, and this was most recently noted in March 2023 when they opted out of attending a party that was thrown for the former TV host in honor of her birthday. While Donald Trump attended and even made a speech for her where he praised her and actually seemed excited to welcome her into the family, Ivanka and Jared declined, citing a scheduling conflict. 

"They were invited to Kimberly's birthday party and were so sad to miss it. Their niece's bat mitzvah was Thursday evening and it had been planned a long time ago," a source told Page Six at the time.

Though it seems many members of the Trump family don't appear to like Kimberly Guilfoyle at all, one person who has gone on record to share their feelings is Eric Trump, Donald Trump, Jr.'s brother. Unlike the other members of the family who are rumored to either outright dislike Guilfoyle or seemingly just tolerate her, he seems to share an opposite view when it comes to the woman who will one day be his sister-in-law. 

In December 2022, following the incident with Ivanka Trump's cropped wedding photo and when rumors were at a fever pitch regarding the family's feelings about Guilfoyle, Eric attempted to put them to rest while attending a party for Toys for Tots at his brother's home. Speaking to Page Six, Eric said that despite the rumors swirling that no one in the family cared for Guilfoyle, it was untrue, and he specifically liked her. "I completely disagree with the narrative and happen to think the world of Kimberly," he said at the time.

He also seemed to try to dispel any questions about whether the family's alleged feelings about Guilfoyle were causing tension with Donald Jr. as well. He told Page Six at the time that he was "best friends" with his older brother and hinted that there is no strife anywhere when it comes to the relationship he shares with the couple as a whole.

It's clear that the Trumps feel a particular way about Kimberly Guilfoyle. "The vibe is that the family doesn't like Kim," a source told Page Six. "She is trying too hard to be in the family." But one family member doesn't seem to mind Guilfoyle.

Lara Trump — Eric Trump's wife — hasn't given any indication that she dislikes Guilfoyle. The first sign that Lara seemed to be okay with her company came in 2021 when the pair were pictured, along with Tiffany Trump, attending a friend's wedding in Florida at the Ocean Reef Club (via the Daily Mail).

Since then, it's been alleged that the women have grown closer following Donald Trump's announcement that he was running for President again in 2024. Though his daughter, Ivanka Trump, was initially one of his biggest supporters, she and her husband, Jared Kushner, have opted to step back from politics this time and won't be part of his campaign or advisory board if he wins a second term. This decision has not sat well with either Guilfoyle or Lara, however, and a source said that they have become more aligned as a result. "Ivanka's decision to stay out of politics and relaunch her brand is another reason she's been keeping her distance. Kimberly, along with Eric's wife, Lara, consider it a huge betrayal, so they've taken sides against her," the source said (via OK!). "No one trusts anyone anymore." 

Tiffany Trump has always been seen as an outlier in her family. Not only did she stay away from joining the Trump family businesses, but she's also a product of Donald Trump's second marriage to actress Marla Maples. As someone who has often been characterized as looking in from the outside, Tiffany can likely sympathize with Kimberly Guilfoyle. Still, that doesn't mean the former Fox News host hasn't annoyed her, especially when it came to her November 2022 wedding to Michael Boulos.

People believed that Ivanka Trump snubbed Guilfoyle when she cropped her out of a family photo at the wedding. However, it could have also been due to Guilfoyle's attire at the event. While Tiffany sparkled in a white wedding dress, she was flanked on both sides by Lara Trump in silver, her mother in lilac, Melania Trump in baby pink, and Ivanka Trump in baby blue. Guilfoyle, who was standing next to Ivanka in the image, opted for a black gown.

According to reports after the wedding, Tiffany was miffed by Guilfoyle's choice of a black dress. Apparently, Guilfoyle knew that there was a dress code featuring pastel colors for women, but chose to just ignore it anyway. "Kimberly wore black, which rubbed everyone the wrong way," a source said (via OK!). "Kimberly knew the dress code and simply disregarded it, which upset both Tiffany and Ivanka."