Everyone Kimberly Guilfoyle Was With Before Don Jr.: Inside Her Rocky Relationship Past

To say that Kimberly Guilfoyle hasn't been lucky in love thus far in her life would be a huge understatement. In December 2024, People confirmed that the former Fox News anchor's messy 6-year relationship with her fiancé Donald Trump Jr. had finally come to an end following months of speculation. The political power couple started with an arguably strong foundation since they apparently knew each other for quite some time before their relationship turned romantic. In fact, Guilfoyle and Don Jr. even snapped a photo with their respective spouses all the way back in 2008. 

It blossomed into something more shortly after Don Jr.'s 12-year marriage to Vanessa Trump ended, since Page Six reported that they had started dating around three months after news of their divorce broke in 2018. A few months later, Page Six revealed one of the weirdest things about Guilfoyle and Don Jr.'s relationship: Their nicknames for each other. A source informed the outlet that the former Fox News host called her beau "Junior Mint" but insisted that it wasn't a nod to his father Donald Trump's wealth. Meanwhile, Don Jr. used to call his partner "Pooh Bear." 

Of course, no number of cutesy nicknames could help us ignore all the glaring red flags in Guilfoyle and Don Jr.'s relationship, like their distance throughout Donald's 2024 presidential campaign, which sadly made the couple's eventual split announcement come as no surprise. In typical fashion, Don Jr. wasted no time in moving on and started officially dating his rumored mistress, Bettina Anderson, shortly after they parted ways. While the president's eldest son may be one of Guilfoyle's most famous exes, he notably isn't the only big name in her relationship history.

While Kimberly Guilfoyle was attending a Democratic fundraiser in 1994, she laid eyes on Gavin Newsom. Although they were both seeing other people at the time, the duo quickly bonded over their unyielding passion for public service and eventually started dating once the opportunity arose. After about seven years together, Guilfoyle and Newsom tied the knot in a lavish ceremony in 2001. Things only seemed to be looking up for them after the well-liked Democratic politician became the mayor of San Francisco in 2003, with the media even dubbing them a power couple. 

However, everything came crashing down in 2005. The couple released a statement to announce they were parting ways after just three years of marriage. In it, Guilfoyle and Newsom blamed their high-pressure jobs for their divorce and insisted that the split was amicable. Later, a confidant acknowledged to the San Francisco Chronicle that the news wasn't all that shocking since Guilfoyle essentially lived out of New York for her work commitments while her then-husband stayed in California. And neither was willing to sacrifice their career to settle on the opposite coast. 

About a month prior to their divorce announcement, Newsom hinted at similar issues during a chat with the Chronicle. "This living on different sides of the continent has taken a huge toll personally. The transcontinental marriage is tough," the San Francisco mayor admitted. "The only godsend is that we don't have kids. You give up your life in the traditional sense." Although those words undoubtedly sounded reasonable at the time, we later learned that there was much more to the situation.

In 2007, the San Francisco Chronicle reported that Gavin Newsom had cheated on Kimberly Guilfoyle with Ruby Rippey-Tourk, his campaign manager and good friend Alex Tourk's wife. Shortly afterward, the Democratic politician confirmed that the unsavory rumors were true and publicly apologized for this grave misstep on his part. While it's unclear whether Guilfoyle was aware of the affair, it's obvious that she and Newsom weren't on as good terms as they claimed — not least because the exes continued to publicly take shots at each other over the years. 

Without referring to her ex-husband by name, the former Fox News host shaded him in her 2022 Turning Points USA speech. "In California, they have vowed to get rid of gas-powered cars with no explanation of how they are going to fund and power alternatives," she pointed out (via Newsweek). "A bunch of winners over there, folks. Ask me how I know." Further, to Guilfoyle, Newsom's political future apparently didn't seem too bright as she also stated, "He ain't making it to the White House." 

During a February 2023 appearance on "The Axe Files" podcast, the governor noted that the Guilfoyle he knew wasn't so staunchly right-leaning. He reckoned that her not-so-stunning political transformation occurred when she first started working at Fox News. However, Newsom assumed that his ex-wife believed she'd changed for the better because of her work on the network. Later in the month, Guilfoyle appeared on "The Charlie Kirk Show" and claimed that Newsom was the one who had switched political gears since he wasn't as much of a leftist during their marriage and didn't have a strong anti-gun stance either.

While Gavin Newsom had a scandalous age-gap romance following his split from Kimberly Guilfoyle, she found love with Eric Villency. They were set up on a blind date in October 2005 and it appears that the couple shared plenty of common ground since Villency was reportedly getting over his own breakup from girlfriend Olivia de Chantecaille at the time. It was a whirlwind romance too, with the businessman popping the question within just two months of dating. However, Guilfoyle and Villency understandably opted to keep their romance under wraps until she was officially out of her marriage to Newsom. 

The happy couple tied the knot in May 2006, only a couple of months after the former Fox News anchor signed off on her divorce papers with Newsom. It was later revealed that Guilfoyle was about five months pregnant when she walked down the aisle. But it's unclear whether this factored into the couple's decision to lock things down so quickly.

While one insider insisted to Page Six, "The wedding was planned long before she learned she was with child," another stated, "[The baby] was the worst-kept secret in town," (via People). Guilfoyle and Villency welcomed their son, Ronan, in October 2006. Then, in 2009, the couple called it quits. Despite everything, though, Guilfoyle's relationship with her ex-husband, Villency, remained strong as they continued to actively co-parent their son.

During a 2015 Mediaite interview, Kimberly Guilfoyle reflected on her two marriages and subsequent divorces, confessing, "I know that from having lost two of the greatest human beings in my life. I would trade any success to have them back." After urging readers to give every relationship their all, the TV personality reminded them to speak up if they felt something was wrong too. Guilfoyle also apparently hinted at what went wrong, cryptically noting, "People can take the easy way out and grow apart." 

She also touched on her relationship with Eric Villency following their divorce, confirming, "I'm still very close with his family. Even when people don't stay married, they can still be a family together." The former Fox News host further detailed how their decision to prioritize their son's happiness had transformed her for the better. And we saw a great example of Villency and Guilfoyle's amicable relationship in May 2018, when she took to Instagram to pat him on the back for doing a great job in an interview. 

Then, in March 2025, Guilfoyle capped off her big day at The White House by reuniting with her ex-husband. After the U.S. ambassador to Greece proudly celebrated her first Greek Independence Day in her new job, she was spotted hanging out with Villency and their son in an Instagram Story, which she later reposted. Naturally, there's also a small chance she shared the Story to make her ex-fiancé Donald Trump Jr. jealous.

Kimberly Guilfoyle's sad relationship history has finally caught up to her. In the immediate aftermath of the politician's past failed romances, she seemingly managed to let go fairly quickly, possibly because Guilfoyle was able to distance herself from her ex-husbands. Unfortunately, with her appointment as the new U.S. ambassador to Greece, she hasn't been able to keep Donald Trump Jr., or his new girlfriend, at arm's length. In fact, she's watched him pack on the PDA with socialite Bettina Anderson on numerous occasions. 

In January 2025, a People source disclosed that Guilfoyle had mixed feelings about her ex-fiancé's new relationship. "Kim is still very fond of Don, and kept a watchful eye out," they noted of her behavior at Donald Trump's 2025 inauguration. "She knows how beautiful and well dressed Bettina is, and there is no question that she was hurt when her romance with Don ended." By then, Guilfoyle had already given us a heartbreaking hint that she can't let go of Don Jr. through her birthday post for him. 

While most people wouldn't bother to publicly wish an ex a happy birthday so soon after their split (or even at all), the former Fox News anchor went all out, sharing an Instagram Story featuring a collage of photos of them together. Thankfully, things were looking up for Guilfoyle around Valentine's Day 2025 since she seemingly hinted at a new romance through an Instagram Story of a bouquet of roses.