All Of The Women Gavin Newsom Dated Before & After Kimberly Guilfoyle

California Governor Gavin Newsom is one of the nation's most high-profile political figures, whose name is often floated as a possible future Democratic presidential nominee. He's politically committed, handsome, wealthy, and he's got a long and storied romantic history dotted with controversies that are compelling without being immediately disqualifying.

One of Newsom's most surprising relationships in retrospect was his four-year marriage to news commentator Kimberly Guilfoyle. Newsom, a staunch Democrat and outspoken critic of former President Donald Trump, married Guilfoyle in December 2001 at a ceremony in a Catholic church on the University of San Francisco campus. Their romance, however, came to an end in January 2005, when they jointly filed for divorce.

Following their split, Guilfoyle went in a very different political direction from her former husband. She became a Fox News personality, she was named a senior advisor to President Trump, and eventually got engaged to Donald Trump Jr. Meanwhile, Newsom went on his own relationship rollercoaster for several years before tying the knot once again with his wife, Jennifer Siebel. However, Newsom's dating timeline -– before and after his romance with Guilfoyle -– is a fascinating look at the governor's heart and mind.

Long before his marriage to Kimberly Guilfoyle and decades before being elected governor of California, Gavin Newsom was serving on the San Francisco Board of Supervisors and he sparked a romance with Kelley Phleger sometime in 1992. The pair's relationship never seemed to get too serious, although they dated for five years before officially calling it quits sometime in 1997.

Interestingly, in 1996, Phleger was at a birthday party honoring the former mayor of San Francisco, Willie Brown, when she crossed paths with actor Don Johnson, who was starring on the hit TV cop show "Nash Bridges." The pair were introduced by producer Jo Schuman Silver, and Johnson reportedly told Silver that he was dead set on dating her. However, Phleger and Newsom were still a couple at the time. After their eventual split the following year, Phleger and Johnson reconnected, and a love connection was forged. Phleger went on to marry Johnson in 1999. The pair are still married and share three children.

In one of the most scandalous moments in his dating timeline, Gavin Newsom, then the mayor of San Francisco, sparked an illicit affair with his appointments secretary, Ruby Rippey Gibney. Rippey Gibney happened to be married at the time to Alex Tourk, Newsom's campaign manager and friend.

The affair came to light when Tourk confronted Newsom about it in 2007 and resigned in disgust as Newsom's chief-of-staff. Soon after, Newsom held a press conference in which he acknowledged the infidelity and apologized for his inappropriate behavior. "Everything you have heard and read is true," Newsom said  (via SF Gate). "I am deeply sorry." While the affair led to Tourk and Rippey Gibney's split, it didn't seem to impact Newsom's political career until the scandal resurfaced during the governor's race in 2018.

Rippey Gibney addressed the incident in a Facebook post in which she said she didn't feel her affair with Newsom should be part of the ongoing #MeToo Movement as it had been used against him by political rivals. "I fully support the #metoo movement. In this particular instance, however, I am doubtful that it applies," she wrote (via The Los Angeles Times). "Yes, I was a subordinate, but I was also a free-thinking, 33-yr old adult married woman & mother."

Gavin Newsom moved on incredibly fast from his marriage to Kimberly Guilfoyle. Not long after it was officially dissolved in February 2006, the then-mayor of San Francisco raised some eyebrows when he was romantically linked with "CSI: Miami" star Sofia Milos. The pair were introduced at former San Francisco Police Commissioner Joe Veronese's wedding that same month. By early March, Newsom and Milos had flown out to Los Angeles together for a nice romantic trip. The pair booked a room at the iconic Chateau Marmont before attending a gala event for an organization co-founded by the Church of Scientology.

Unsurprisingly, this led to some political backlash from critics of Scientology, who began to slam the mayor on social media and question whether or not he'd joined the organization. Newsom shot down the rumors at the time, telling reporters during a press conference (via SFGate): "I think the only thing to be concerned about is the absurdity of the whole thing and the fact that people would be taking these things so seriously... My gosh, folks, Relax. I'm a practicing Irish Catholic. I'm not a Scientologist, and I couldn't tell you two things about it." The drama around Milos' connections to the Church of Scientology, however, seemed to cut short any potential romance between the pair.

Later in 2006, Gavin Newsom courted controversy once again when he allegedly began courting a 19-year-old aspiring model named Brittanie Mountz. The romance drew criticism over their age difference, as Newsom was 38 at the time. Some also found the discrepancy in their positions of power to be a concern, as Mountz was a restaurant hostess who had just graduated college and Newsom was the mayor of San Francisco.

Their purported relationship faced multiple potential scandals, beginning with a photo of Mountz — who was under the legal drinking age — holding a glass of wine at an event she attended with Newsom. A spokesperson for Newsom said in a statement (via SFGate) that the mayor wasn't responsible adding, "If she was drinking, the mayor didn't notice." Additionally, it seemed that Mountz had tried to conceal how young she actually was, reportedly changing her age on her MySpace page from 19 to 26. Interestingly, Mountz was a registered Republican.

In September 2006, an aggravated Newsom berated reporters for their coverage of his relationship, complaining to the press that he's had to "deal with all kinds of terrible calls from reporters doing horrible things that are mean-spirited." Newsom maintained that he'd never actually dated Mountz, but instead had been unfairly linked to her simply because they'd attended several events together.

Gavin Newsom seemingly found his true love when he began dating film director and actress Jennifer Siebel, after hitting it off on a blind date in late 2006. The pair began their relationship amid the drama and fallout surrounding Newsom's affair with Ruby Rippey Gibney and continued as Newsom sought treatment for alcohol abuse in February 2007.

Newsom proposed to Siebel in January 2008, and the happy couple went on to exchange vows that July at a ceremony on a ranch in Stevensville, Montana. The following year, they welcomed their first child together — a daughter appropriately named Montana. The happy couple shares four children; they have another daughter, Brooklynn, as well as sons Dutch and Hunter.

Newsom was elected governor in November 2018, and Siebel has been an active "first partner" — a term Siebel coined — ever since. She's been outspoken about her appreciation for her husband's love and support, telling the Nob Hill Gazette in March 2024, "All of us got to, or are getting to, where we are, yes, through our own hard work and grit, and resilience and determination – and through partnership, where someone's holding us and making life easier for us, so that we can shine and be our best self."