Inside Gavin Newsom's Tragic Relationship History (Including Kimberly Guilfoyle)

If U.S. politics had a hot list, Gavin Newsom would undoubtedly be a permanent fixture at the top. In fact, a 2010 New York Daily News poll found that 33% of Americans had a crush on the California governor. But for those hoping for a chance, sorry — he’s happily married. His dating history, however? Not exactly flawless. After all, it includes Kimberly Guilfoyle, which isn’t something Newsom likely brags about.

These days, though, Newsom seems to have finally gotten it right with Jennifer Siebel, whom he married in 2008. Their love story started with a blind date that turned out to be a perfect match. “We had so much in common, we were blown away — from our love for Africa to our interests in political issues to art and the wine business and college sports,” Siebel told The San Francisco Chronicle (via SFGate). Since then, they’ve built a life together, raising four kids: Montana, Brooklynn, Hunter, and Dutch. Siebel is also actively supporting Newsom in all his political endeavors and takes her job as first partner very seriously. “I think for me, the hardest part [of the job] is I’m also my husband’s partner, the first person he talks to in the morning, even if we’re mumbling, and the last person at night,” she explained to Nob Hill Gazette. “So part of my role, and I don’t always do a great job of it, full disclosure, is holding him and supporting him.”

From the looks of it, Newsom struck gold with Siebel, but before they got together, there’s no denying that he made some questionable relationship choices — including a four-year marriage to Guilfoyle and, just for extra spice, an affair with a subordinate. His romantic history is anything but boring, and dare we say tragic like his life?

Gavin Newsom’s first public relationship (well, sort of) was with Kelley Phleger back in the 1990s. At the time, Newsom was a San Francisco Board of Supervisors member, and things were serious — so serious that they even bought a house together, per SFGate. But the love nest didn’t last long. In fact, it is even believed to have gone unoccupied altogether. Newsom asked Phleger for a break, she agreed, and soon after, their relationship was history.

What he didn’t see coming? Phleger moving on with a man who had been eyeing her the whole time. As it turns out, “Miami Vice” and “Nash Bridges” star Don Johnson (yes, that’s also Melanie Griffith’s ex-husband and Dakota Johnson’s dad) had been lurking in the wings, shooting his shot whenever he got the chance — even while she was still with Newsom. And well, let’s just say that his persistence paid off. By fall 1997 — mere months after her breakup — Phleger and Johnson were officially an item. By April 1998, they were engaged, and by 1999, they were married. Up to this day, they’re still going strong with three kids in tow.

As for Newsom? Who knows how he took it, but considering he was busy with his re-election campaign — and later became mayor and dated other high-profile women — it’s safe to assume he survived just fine.

We all have that one ex we’d rather erase from our dating history, and for Gavin Newsom, that dubious honor probably goes to Kimberly Guilfoyle. To be fair, this was long before she went full MAGA and became unrecognizable from all the cosmetic tweaks. Back in the early 2000s, Newsom and Guilfoyle were actually a power couple — married from 2001 to 2006 and even dubbed the “new Kennedys” at one point. But their marriage was far from picture-perfect. With Newsom focused on his mayorship and Guilfoyle chasing a broadcasting career, they spent more time apart than together. “The transcontinental marriage is tough,” Newsom told the San Francisco Chronicle in December 2004 (via SFGate). “The only godsend is that we don’t have kids. You give up your life in the traditional sense.”

Shocking no one, the marriage fell apart. They announced their split in early 2005, blaming their demanding jobs. “Over the past 10 years, we have developed a tremendous bond of love and respect for each other,” they said in a statement at the time. “That will never change.” Except that it did change. Their divorce was finalized in 2006, and from there, they took wildly different paths. Newsom climbed the political ladder to become California’s governor, while Guilfoyle cozied up to the far right, working at Fox News and later for a Trump super PAC. And just to make things even messier, she got engaged to Donald Trump Jr.

As for where they stand now? Newsom has taken some shady public digs at Guilfoyle. When asked if he still talks to his ex on MSNBC‘s “Alex Wagner Tonight,” his response was a flat “nope. Not lately.” And when asked if he finds it “weird” that Guilfoyle is practically part of the Trump dynasty now? “Yeah, of course.”

Gavin Newsom’s divorce from Kimberly Guilfoyle must have hit hard, because he went on to do something that nearly torpedoed his political career. Not long after their split, Newsom had an affair with Ruby Rippey-Tourk — who just so happened to be the wife of his then-deputy chief of staff, Alex Tourk. Oh, and she also worked for him as his appointment secretary at the time. Messy doesn’t even begin to cover it.

The affair itself happened around mid-2005, while Newsom and Guilfoyle were still finalizing their divorce, but it didn’t become public knowledge until 2007. That’s when Ruby, as part of a rehab program, came clean to her husband — who promptly resigned from his post. Newsom had no choice but to face the music, calling a press conference to confirm what everyone already suspected. “Everything you’ve heard and read is true. And I am deeply sorry about that,” he admitted, per The New York Times. “I’ve hurt someone I care deeply about, Alex Tourk. And that is something I have to live with.”

Naturally, the scandal followed him for years, especially when he made his bid for governor. But to his credit, he didn’t try to sweep it under the rug. He owned up to it — again and again. “I would say the same thing that I said (then) to the voters in San Francisco. That I acknowledged it. I apologized for it. I learned an enormous amount from it,” he said in 2018, per the San Francisco Chronicle. “And I am every day trying to be a champion and a model — not just for women and girls — but to deal with the issue that we need to focus on, which is the crisis with men and boys in this state and in this country.”

As if an affair wasn’t enough drama, Gavin Newsom went on to spark even more controversy with his next romance — this time with “CSI: Miami” cast member Sofia Milos. The issue? Milos was a devout Scientologist, which naturally had people wondering if Newsom was dabbling in the controversial religion, too.

But Newsom, never one to let a rumor spiral out of control, shut it down fast. He swore he didn’t have anything to do with Scientology and brushed the issue off as something out of the realm of possibility. “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,” he told reporters at the time, per CT Insider. “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.'”

And as it turns out, no one needed to worry — because the romance fizzled out just as quickly as it started. It doesn’t seem like either of them took it all that seriously, but they did have fun while it lasted. “We are getting to know each other and are dating like any two people would,” Milos told The New York Times when asked about their relationship in 2006. “We just love spending time with each other whenever we can and as often as we can as there is an immense amount of mutual respect and affinity.”

Gavin Newsom sure has a talent for finding himself in messy situations. After his affair scandal and relationship with Sofia Silos, his next rumored romance raised more than a few eyebrows once more — this time, with someone nearly two decades younger than him. He was reported to have dated Brittanie Mountz, a college student at Sonoma State University who was just 19 when their supposed tryst started (though she did turn 20 a month before Newsom hit 39, if that makes it any better).

Things only got weirder from there. According to The San Francisco Chronicle, Mountz had mysteriously adjusted her MySpace age from 19 to 26 around the time that they were reported to be an item. To make things sketchier, she was spotted sipping wine at an event Newsom attended, sparking questions about whether he was cool with underage drinking. His spokesperson, however, came to the rescue, telling the outlet, “Brittanie is a friend of the mayor’s. They did not attend the Bloomingdale’s event together. Obviously there has been some uncertainty about her age. However, given what The Chronicle has dug up on her, if she was in fact drinking, that is a mistake.”

So, were they actually just friends? Hard to say, considering they attended a San Francisco Symphony concert together and even walked the red carpet as a pair. But here’s the real kicker: Mountz was a registered Republican. Newsom, a die-hard Democrat, dating a Republican? Maybe that was the biggest scandal of all.