How Does Vanessa Trump Feel About Kimberly Guilfoyle? Here's What We Know

After Vanessa Trump's messy divorce from Donald Trump Jr., the former model opted to keep her private life out of the media spotlight for the most part. The two were married for 12 years and welcomed five children during their time together. Yet, months before their divorce was finalized in late 2018, Donald Trump's eldest son was already back swimming in the dating pool. Donald Jr. was first linked to San Francisco's former prosecuting attorney, Kimberly Guilfoyle, as early as May 2018, when an insider told Page Six, "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."

Given the Trumps' high-profile status and constant media exposure, it was only a matter of time before people started wondering how Vanessa felt about Guilfoyle. While the former lawyer didn't have a role in Donald Jr. and Vanessa's marriage crumbling, she was friends with them when they were a couple. Despite this, Vanessa seems unfazed by their romance and even defended Guilfoyle when she began dating her then-estranged husband.

In an August 2018 interview with The Washington Post, Kimberly Guilfoyle revealed that she and Donald Trump Jr. had first met at least a decade before they started dating. Apparently, they initially connected through mutual friends and stayed in touch because their respective eldest children attended the same school. Over the years, they were photographed together on multiple occasions, but always in the presence of Vanessa Trump. Notably, Guilfoyle was married to Eric Villency at the time.

Despite the unconventional dynamic of a friend dating one's ex-husband, Vanessa didn't seem to have a problem with it. When Guilfoyle faced criticism for her relationship with Donald Jr., including calls for her dismissal from Fox News, Vanessa decided to step in. Taking to X, formerly Twitter, Vanessa reposted Don Jr.'s tweet condemning the backlash against Guilfoyle and wrote, "The lengths people will go to attack a woman simply because she's dating Don." She continued, "We've been separated for over [nine] months and respect each other's decisions [and] privacy. We'll focus on raising our great kids. Would be nice if the press did the same rather than obsess over our [private] lives!"

Guilfoyle, on the other hand, refrained from making any public statements about Vanessa. Still, their amicable relationship was evident when they were seen standing next to each other at Ivana Trump's funeral in 2022, proving there's no bad blood between them.

While Vanessa Trump appears to have no issues with Donald Trump Jr.'s partner, the rest of the Trumps reportedly don't feel the same way about Kimberly Guilfoyle. Despite getting engaged to Don Jr. in 2020, Guilfoyle apparently hasn't garnered much sympathy from some of her fiance's siblings.

According to a source cited by OK! Magazine, both Ivanka and Tiffany Trump are unimpressed with Guilfoyle. "Ivanka doesn't trust her because she sees her as a social climber desperate to marry into the family," the insider stated. Meanwhile, Tiffany allegedly had a problem with Guilfoyle's attire at her 2022 wedding. "Kimberly wore black, which rubbed everyone the wrong way. [She] knew the dress code and simply disregarded it, which upset both Tiffany and Ivanka."

The speculation about the Trumps' animosity towards Guilfoyle was seemingly confirmed when Ivanka brutally cropped her out of an Instagram photo from Tiffany's wedding. However, after the media picked up on the shady move, Ivanka reposted the unaltered version, including Guilfoyle, to her Instagram Stories. So, even though Vanessa doesn't seem to hold any grudges against her ex-husband's beau, other members of the Trump clan might be doing just that.