Kimberly Guilfoyle's Relationship Résumé Reads Like A List Of Red Flags

Kimberly Guilfoyle and Donald Trump Jr.'s best efforts to convince everyone that their relationship ended amicably have been in vain. A few weeks after news of their split broke, Guilfoyle shared a birthday post for Don Jr. that served as a heartbreaking hint that she couldn't let go. The former Fox News anchor was apparently reminiscing about their relationship on the big day as she shared a collage of photos from happier times on her Instagram Story. 

She put on a similar display for Eric Trump's birthday just a few days later, sharing another Instagram Story featuring a photo of her with her ex and his family. Guilfoyle's photo selection felt even more awkward given that Eric was at the edge of the frame while Don Jr. was front and center. Needless to say, Donald Trump's eldest son wasn't swayed by her little reminders about their romance, continuing to flaunt his new relationship with Bettina Anderson. 

In February, Anderson subtly flexed on Guilfoyle by sharing her lavish Valentine's Day plans. Of course, the TV personality wasn't going to let that slide. A few days after it went live, the Trump staffer tried to show that she had moved on herself by sharing a photo of a bouquet of roses, again to her Instagram Story. Unfortunately, the timing of the post was yet another reminder that she wasn't entirely over her ex. However, if Guilfoyle does have a new man in her life, he should wary of more than just her supposed inability to let go of her past relationship.

One of the strangest things about Kimberly Guilfoyle's marriage to Gavin Newsom is that they lived on opposite coasts most of the time. According to an SF Gate source, the media personality's job with Court TV kept her glued to New York, while his position as the mayor of San Francisco understandably prevented Newsom from being away from the west coast for too long. Needless to say, the couple's unconventional arrangement gave rise to a lot of curiosity. However, when SF Gate brought up the public scrutiny in a 2004 interview with Guilfoyle, she insisted that they made it work.

"Why can't a couple have two major careers? And why is it weird for the woman to be the bicoastal one? Men do it all the time!" the former Fox News host asserted. Additionally, she believed those who were questioning their happy union ought to focus more on their own romantic relationships. On the other hand, Newsom didn't shy away from acknowledging that an intercoastal marriage could be mentally taxing in a 2004 interview with the San Francisco Chronicle. 

The then-mayor of San Francisco was glad they didn't have kids because they would have only complicated their odd living arrangement even further. Ultimately, though, Guilfoyle and Newsom blamed their demanding careers for their divorce in a statement shared in January 2005. At the time, a confidant of the couple told the SF Gate that the end of their 3-year marriage seemed inevitable since "they [had] been leading separate lives" due to all the time spent apart.

Kimberly Guilfoyle's inability to choose her words carefully when she's dating public figures has led to several awkward moments over the years. The former mayor's first wife made a splash at an awards ceremony for the Empire State Pride Agenda Foundation in October 2004 for all the wrong reasons. According to the NY Post, after acknowledging Gavin Newsom's dashing looks, she quipped, "Is he hung? Yeah," (via SF Gate). Somewhat surprisingly, that wasn't the former Fox News host's most embarrassing moment of the night as she quickly followed it up with: "Is he (she waved her hand to suggest gay)? Not unless you can give a better" while pretending to eat a banana. Later, Guilfoyle insisted that the punchline of the joke was "Not unless you are better than me," and she hadn't made a lewd gesture but only given a thumbs up.  

Of course, as time went by and she gradually grew more vocal in her support for Donald Trump, Guilfoyle's opinions of the Democratic politician drastically changed. Speaking at Turning Point's ultra conservative event America Fest, in 2022, the future White House staffer shaded her ex-husband without name-dropping him, only referring to Newsom's apparent desire to significantly reduce gas-powered car usage by snarking simply, "He ain't making it to the White House," (via Newsweek). In January 2025, Guilfoyle took another shady dig at Newsom as Trump launched his own brutal nickname for him. In a Truth Social rant about the California Governor's handling of the wildfires in the state, the outspoken leader referred to him as "Gavin Newscum." And Guilfoyle proudly showed her support by sharing a screenshot of it on Instagram.

Gavin Newsom and Kimberly Guilfoyle both moved on incredibly fast after their marriage. But the former Fox News host took it to a whole other level, according to reports combined by People. Although Guilfoyle's relationship with Eric Villency began when they were set up on a blind date in October 2005, they were clearly completely smitten with each other because he popped the question after only about a month or two of courtship. However, they agreed to keep their romance private until her divorce from Newsom was finalized.

Their fast-moving relationship only seemed more questionable considering the fact that Villency was also fresh out of a relationship with Olivia de Chantecaille when they first met. Nevertheless, the businessman and the political commentator tied the knot in May 2006. At the time, an insider claimed that Guilfoyle's not-so-secret pregnancy may have compelled them to accelerate their wedding plans. However, another source insisted that everything had been set in motion long before she learned she was expecting the couple's first child. 

In October 2006, Villency and Guilfoyle's son, Ronan Anthony, was born. Sadly, the media personality's second marriage wasn't built to last either, and they parted ways in 2009. In a 2015 Mediaite interview, Guilfoyle revealed that she still shared a good relationship with her second ex-husband and his family. After labeling Newsom and Villency "two of the greatest human beings in my life," the former Fox News host reflected on the end of her two marriages, reasoning, "With marriages, people can take the easy way out and grow apart. Or you can show respect and loyalty and that's what I've tried to do in all my relationships."

Although Kimberly Guilfoyle has taken her support of Donald Trump too far several times, she has still been unsuccessful in getting into the family's good books. According to a 2019 report by The Atlantic, the Trump clan put on a show of friendliness around the former Fox News anchor but they weren't actually too fond of her. A source disclosed that they were unhappy with the former Fox News anchor's presence at the White House Fourth of July party because she overshadowed Ivanka Trump and Jared Kushner. 

Although Donald had made many comments about Guilfoyle's beauty in the past and even inquired if she was single, he still wasn't supportive of her bid to become the White House Press Secretary during his first administration. "Even he can tell the difference between the attractive women on Fox who have a little bit of substance, and those who will be derided as airheads," an insider explained. Given all this, it's unsurprising that Donald Trump Jr. may have chosen his next partner with his family's preferences in mind. 

In December 2024, a source divulged to People that the businessman was pleased that his father would see him in a better light for getting involved with someone like Bettina Anderson. They also revealed a point of contention between Don Jr. and his ex by dishing, "Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual." Likewise, another People insider claimed that Guilfoyle was fame-obsessed.

In 2007, around a year after Kimberly Guilfoyle and Gavin Newsom finally signed off on their divorce papers, the SF Gate reported that the politician had cheated on his then-wife with Ruby Rippey-Tourk, who was actually Newsom's campaign manager's wife. Shortly afterward, the staunch Democrat confirmed that he had indeed had an affair with Rippey-Tourk. Although there's no way of knowing if Guilfoyle was aware of his infidelity before their split, it should have turned her off getting involved with cheaters. However, she still got into a relationship with Donald Trump Jr., who had reportedly cheated on his ex-wife, Vanessa Trump, with Aubrey O'Day. 

Then, in August 2024, history started repeating itself when the president's eldest son was spotted out and about on several intimate hangouts with Palm Beach model and socialite Bettina Anderson. At the time, an insider shared Guilfoyle's feelings with the Daily Mail: "Kimberly either didn't know about Bettina — or didn't want to know." They elaborated, "She's no fool but it's easy to deceive yourself when you're so committed to someone and believe he's committed to you." 

In December 2024, shortly before news of Guilfoyle and Don Jr.'s split broke, a source confessed to to People that he had already been dating Anderson for nearly six months. But, "For the most part Kim has looked the other way because she loves the power and lifestyle." With all these highly publicized relationships and red flags, it seems the U.S. ambassador to Greece may have trouble finding a partner. And yet, our matchmaker has a good idea of who Guilfoyle should date in 2025.