Kimberly Guilfoyle And Vanessa Trump's Similar Pasts Prove Don Jr. Has A Type

One major thing that Kimberly Guilfoyle and Vanessa Trump have in common is that both women have been in romantic relationships with Donald Trump Jr. Vanessa and Don Jr. got together in the early 2000s and were married from 2005 to 2018. The same year that their marriage ended, Don Jr. and Guilfoyle's relationship went from platonic to romantic. The pair had been friends since 2007, and photographic evidence from that time actually shows the former Fox News host hanging out with Vanessa and Don Jr. A year later, Guilfoyle and the Trumps were even involved in a double date situation, when she brought her then-husband Eric Villency to join in the fun. 

A major part of the two couples' connection came from the fact that their kids went to school together. Vannessa even put in a kind word for Guilfoyle just a few months after she and Don Jr. got divorced. "The lengths people will go to attack a woman simply because she's dating Don," Vanessa proclaimed on X, formerly known as Twitter, following a media brouhaha over their burgeoning romance. "We've been separated for over 9 months and respect each other's decisions & privacy." Although it's not clear how chummy the two women are currently, they have a surprising amount of common ground, which could be part of the reason Don Jr. was attracted to both.

First and foremost, it's worth noting that both Vanessa Trump and Kimberly Guilfoyle spent some time modeling at one point. In Vanessa's case, she started out in the business as a kid. While it's not clear who represented Vanessa back then, her mom did work on the agency side of the industry. As an adult, Vanessa continued her modeling career, with jobs that took her all the way to Australia. In contrast, Guilfoyle's stint in the fashion industry was the result of happenstance. Guilfoyle felt modeling was an appealing venture salary-wise, and in part, it helped finance her law degree. She worked for big name clients like Macy's and Victoria's Secret, informing Cosmopolitan in 2014, "I was able to meet a tremendous [number] of interesting people through modeling, and I really learned a lot about self-confidence and self-esteem."

She continued, "I learned how to cue into my own autonomy as a woman." However, modeling was just one of many jobs on Guilfoyle's lengthy résumé, since she went on to become a teacher, lawyer, and TV broadcaster for various outlets, including CNN and Fox News. This wasn't the only time Guilfoyle worked in front of the camera either. In 2004, she played a small role as a lawyer in the movie "Happily Ever After." Likewise, Vanessa has a single acting credit to her name. In 2003, she had a cameo in "Something's Gotta Give" where she was simply credited as "Beauty."

Another crucial area where Kimberley Guilfoyle and Vanessa Trump are quite similar is with their approach to motherhood. Guilfoyle has one child, Ronan Villency, with her former husband while Vanessa Trump is mom to five kids from her marriage to Donald Trump Jr. Both women have consistently demonstrated their desire to prioritize their children as their two families come together. In the same post on X where Vanessa supported Don Jr. and Guilfoyle's then-new romance, she also discussed the continuing goal of her relationship with her ex-husband, confirming, "We'll focus on raising our great kids." Vanessa's byline on the platform also states, "My children are my life!" To that end, many of her posts are photo updates featuring her growing brood. 

During the early days of the COVID-19 pandemic, she also mentioned the challenges of meeting five different kids' needs while also homeschooling them. Over on Instagram, Guilfoyle has also shared several sentimental posts about her son. When Ronan turned 17, she wrote (using phrasing very similar to Vanessa's), "You are my life and my most enduring love." In addition, the former Fox News host also posted photos of herself on an outing with Don Jr. and his other children, sweetly referring to them as "our kids." Since they were living with Vanessa in Florida, Guilfoyle and Don Jr. decided to move there, too. She takes the idea of a blended family very seriously, collectively describing them as "The Donberly Bunch" in a 2018 interview with The Washington Post.