Kimberly Guilfoyle's Dating History Explained

It's hard to tell what qualifies a person for inclusion in the Trump crew. Some of those who married in, like Melania Trump and Jared Kushner, have a quiet demeanor and statuesque height in common. Meanwhile, political aides like Steve Bannon and Roger Stone seem to share a fiery, "Zelig"-like history. But where does Donald Trump Jr.'s partner Kimberly Guilfoyle fit into the family ethos?

Well, for starters, she shares a history as a model and involvement in the pageant world with Ivanka Trump and Donald Trump Sr., respectively. Like many in the former Trump administration, she's also done time at Fox News. On top of those similarities, Guilfoyle was long presumed to be of one political ideology when in actuality, she was another. This is something the former president can likely relate to, with Newsweek accusing him of "political promiscuity" in allegedly switching between Democrat and Republican since the early '00s. 

But perhaps the biggest commonality Guilfoyle shares with the Trump clan is her colorful dating history. Similar to Trump Sr., she's had three very public marriages, and those relationships and divorces have resulted in plenty of headlines. As her dating history may strangely suggest, Guilfoyle has more in common with her boyfriend's dad than the general public might think. 

From an apparent Democrat to a MAGA hat

When Kimberly Guilfoyle made her debut as Donald Trump Jr.'s paramour, most people likely recognized her as a Fox News talking head. Californians, however, might have remembered her as San Francisco's former First Lady, and they may have scratched their heads. Once upon a time, Guilfoyle was considered what Washington Post described as "one half of a liberal power couple" in the Sunshine State. 

Gavin Newsom, the current governor of California, was once mayor of San Francisco, and Guilfoyle was his wife. In 2004, Newsom made waves with the supremely liberal decision to grant marriage licenses to same-sex couples even though it was illegal at the state level, per CNN. The couple was so young, attractive, and seemingly Democratic that Harper's Bazaar even christened them "The New Kennedys," per SF Gate

But it turned out Guilfoyle wasn't so liberal after all. In 2018, she made the surprising admission to Washington Post that she's actually been a registered Republican since she was 18. A senior Trump advisor allegedly told Insider that nowadays she and Trump Jr. "are like the prom king and queen of MAGA land."

Kimberly Guilfoyle's career has been interesting

Kimberly Guilfoyle shares a history of lingerie modeling with Donald Trump Sr.'s wife and former First Lady Melania Trump. According to Insider, she posed for the catalogs of both Macy's and Victoria's Secret, and the gigs helped pay her college and law school tuition.

"I knew I wanted to go to law school, and I wanted to have the funds to do so," she told Cosmopolitan. She explained that modeling was instructional for her sense of "self-confidence and self-esteem" and that she appreciated the value of the opportunity. "I learned how to cue into my own autonomy as a woman," Guilfoyle told the outlet. "I don't have any regrets about all of the jobs in the different fields that I've worked in."

She also worked for district attorneys in both Los Angeles and San Francisco, per the Washington Post. Of her time there, former colleague Paul Cummins said, "She was a down-to-earth, classy prosecutor." Per the outlet, Guilfoyle made a name for herself through high-profile and dangerous city cases while being considered part of "the city's glitterati."

The good wife

In 2001, Kimberly Guilfoyle and Gavin Newsom got married, having met years later while she was working in the district attorney's office, and he was rising in county government, as the couple shared on "Charlie Rose." The San Francisco Chronicle called their wedding "the social event of the year," per the Los Angeles Times. Meanwhile, SF Gate described the "lavish reception" as a scene of "splendor."

Newsom became mayor of San Francisco in 2004 and served in the office until 2010. Guilfoyle was by his side as First Lady for the first few years, even hosting Prince Charles and Camilla, Duchess of Cornwall, when they visited San Francisco. "I spent three days with them, and it was a wonderful experience," she told People. "During one of the formal dinners, I was sat next to Prince Charles who was kind enough to share the rest of his apple tart dessert with me."

But her time in the Mayor's Mansion would be short-lived: Guilfoyle and Newsom divorced a little more than a year into his first term.

Newsom's alleged affair ended their marriage

Although Gavin Newsom and Kimberly Guilfoyle were hailed as a new Democratic power couple, their bicoastal marriage dissolved shortly after he took office as San Francisco mayor. Per, Washington Post those who knew the couple alleged that they treated "each step of their careers, and each other, as a means to an end." As reported by the outlet, Guilfoyle started a new television job based in New York City just after Newsom was sworn in which, at the very least, put a distance between them. 

Then, there were the rumors of Newsom's affair with his campaign manager's wife, Ruby Rippey-Tourk. A fact which the governor confirmed during a 2007 news conference, saying, "Everything you've heard and read is true. And I am deeply sorry about that." Originally, Guilfoyle and Newsom's split was attributed to "the demands of our respective careers." 

Guilfoyle has never spoken about the alleged infidelity, but she didn't mince words years later when she gave a speech at the Republican National Convention in 2020. "If you want to see the Socialist Biden/Harris future for our country, just take a look at California," she said, referring to the state where her ex-husband was sitting as governor at the time. "It is a place of immense wealth, immeasurable innovation, an immaculate environment, and the Democrats turned it into a land of discarded heroin needles in parks, riots in streets and blackouts in homes." Irreconcilable differences, indeed.

Guilfoyle's dad was an advisor to Newsom

During an emotional moment on "The View" in 2019, Kimberly Guilfoyle shared her heartbreak at having "lost both" her parents to cancer. The former Fox News host opened up about her experience while sympathizing with co-host Megan McCain over her own late father, politician John McCain. "I considered him my friend. I miss him," she said of John, and added of her own parents, "I understand your loss. Yesterday was the anniversary of my mother passing. I lost my father Thanksgiving night." Per the Daily Mail, Guilfoyle's mother died when Kimberly was only 11, and her father, Anthony Guilfoyle, followed in 2008.

Like her first husband, card-carrying Republican Kimberly's father was a Democrat. In fact, he acted as a political advisor for Gavin Newsom while Kimberly was married to him and even after their divorce. After his death, Anthony was called "an indelible fixture on San Francisco's political scene" in an SF Gate obituary. The outlet also described him as having become an "entrenched member of Gavin Newsom's inner circle" and noted that some knew him as "The Godfather."

"He was the one who took care of everybody," Kimberly told SF Gate. "He was the communicator. He ran the back channels ... He was a key adviser to Gavin, talking to him about San Francisco, telling him who you can trust, giving him the measure of a person's integrity."

Her second husband was a furniture scion

Kimberly Guilfoyle moved on from her 2005 divorce relatively quickly, remarrying in May 2006, per The New York Times. Her second husband was Eric Villency, the CEO of Maurice Villency, a furniture chain that his grandfather had founded. Like Guilfoyle, he was also a former model, though he's perhaps best known today as the guy who invented the SoulCycle bike

Guilfoyle and Villency welcomed a son named Ronan in 2006, and their marriage ended almost three years later. Speaking to The List, divorce lawyer Christina Previte speculated that it was likely that the couple may have signed a pre-nuptial agreement, potentially leaving Guilfoyle without access to Villency's family fortune post-split. Their divorce didn't receive much media coverage and was much less scandalous than her split from Gavin Newsom.

Despite Guilfoyle having now moved on in a very public manner, the former couple is on good terms. Guilfoyle even comments heart emojis on Villency's Instagram photos with their son.

How Kimberly met Donald

Kimberly Guilfoyle reportedly met her next long-term partner, Donald Trump Jr., through mutual friends at a party, per the Washington Post. Incidentally, Guilfoyle's son and Trump's daughter went to the same school, but they didn't start dating until years later. 

Trump Jr. was married to his first wife, Vanessa, until 2018. However, just as it seems with Guilfoyle and Eric Villency, it would appear that there is no beef between them. There are even photos of Guilfoyle and Trump posing with their respective former spouses at a party. After Trump Jr.'s divorce was announced, Page Six broke the news that he and Guilfoyle were dating after they were spotted sticking "close to each other" at a party.

​​"Don Jr. and Kimberly are seeing each other and are having a great time," a source told the outlet. "While he wants to respect the privacy of his family, he is getting divorced, and he enjoys Kimberly's company." At the time, Guilfoyle was a co-host of "The Five" on Fox News. She later left the network amid claims she had sexually harassed an assistant, which Guilfoyle denied, per CNN.

A romance intersecting with politics

When Kimberly Guilfoyle and Donald Trump Jr. started their relationship, his father was already in the Oval Office. And rather than keep their respective governmental connections separate from their romance, the couple seemed to embrace public life as a political couple. In fact, part of what drew Trump to Guilfoyle was her on-air support of his father's presidential campaign, per the Washington Post. "When everyone else said that Hillary was unstoppable, Kimberly stood firmly with my father," he said.

Only a month after their relationship became public, they attended the Montana Republican Convention together, with Trump Jr. even mentioning Guilfoyle by name in a speech, according to Vanity Fair. They attended many more political events together, sometimes locking lips onstage. The appearances culminated in Guilfoyle's notoriously fiery speech at the Republican National Convention in 2020, described by The Cut as "Kimberly Guilfoyle Yell[ing] Into the Void." Many memes were made.

They share an enviable real estate portfolio

When Kimberly Guilfoyle and Donald Trump Jr. aren't making speeches on the campaign trail, they're snapping up impressive pieces of real estate. In 2019, they bought a home in the Hamptons together after just a year of dating, per Insider. The home is located in Bridgehampton and boasts seven bedrooms, plus waterfront access.

They sold the house for $8.14 million a year later, having originally paid $4.4 million for it, meaning it almost doubled in value while they owned it. Soon after that sale, they picked up a $9.7 million mansion in Jupiter, Florida, close to Trump Jr.'s father's Mar-a-Lago resort in Palm Beach, according to People. The Trumps, as a whole, embarked on a mass exodus to Florida after Donald Trump Sr. failed to secure a second term as president. Trump Jr. and Guilfoyle should have plenty of company in their enormous new house, at the very least.

Newsom seems perplexed by Guilfoyle's political shift

Since Kimberly Guilfoyle and Gavin Newsom broke up in 2005, he's had quite the career trajectory. After serving five more years as Mayor of San Francisco, he later became Governor of California. Lily Jamali, a reporter for KQED, asked the Democratic Newsom about his strange connection to the Trumps in September 2018. "I think in those terms, I'm still trying to come to grips with all of it," he responded and is said to have "chuckled" as he did so, "No, it's fine. I wish her well and them well. And we see the world, clearly, with a different set of eyes politically."

Back in 2004, during an appearance on "Charlie Rose," Guilfoyle had kind words for her then-husband's budding political career, saying, "I knew that he had ... the vision and discipline, and as it's turned out, the courage to be in politics to do the right thing." However, years later, Newsom and Donald Trump Sr. traded barbs. And although the California governor had benign words for Guilfoyle, she called Newsom's state of California out as an example of government policies gone bad during a speech at the 2020 Republican National Convention. 

Donald Trump Jr.'s ex-wife has no beef with Guilfoyle

With a combined six children and three ex-spouses, it's safe to say that both Donald Trump Jr. and Kimberly Guilfoyle have a past. And while Guilfoyle has a publicly amicable relationship with her child's father, Eric Villency, it seems Trump Jr. and his ex-wife Vanessa Trump are just as friendly. Despite the timeline, Guilfoyle and Vanessa's relationships with Trump Jr. didn't overlap. Vanessa filed for divorce in March 2018, while Trump Jr. and Guilfoyle were first seen together a month later, per People. There seems to be no bad blood between any of them.

Vanessa stuck up for Guilfoyle on Twitter in June 2018, after pundits called for her firing from Fox News due to the fact that she was dating Trump Jr. "The lengths people will go to attack a woman simply because she's dating Don," Vanessa tweeted. "We've been separated for over 9 months and respect each other's decisions & privacy." Also, Vanessa "liked" a few of Trump Jr.'s tweets even after their separation, per People. That's despite the fact that, according to The New York Times, her family is believed to be more liberal than the Trumps are.

Did Guilfoyle and Trump Jr. put a ring on it?

Per the Daily Mail, Donald Trump Jr. and Kimberly Guilfoyle were thought to have announced their engagement at the start of 2022, and the timing was perfect for it. Trump Jr's divorce was now finalized, and the couple had seemingly taken a break from campaigning. Not many details are known about the proposal or any wedding plans, but a source told the outlet, "Kim has been wearing her engagement ring, and both are very excited about blending their families."

Eagle-eyed Instagram followers had spotted a diamond on her left ring finger in a Christmas post from January 1, 2022, per People. The outlet suggested that the picture — which was posted on New Year's Day — was snapped at Mar-a-Lago in front of a festive Christmas tree. A month later, Guilfoyle tussled with the congressional committee tasked with investigating the January 6 invasion of the U.S. Capitol building. It seems pretty clear that the couple's political lives and romance will remain intertwined for as long as they're together.