The Affair That Rocked Kimberly Guilfoyle And Gavin Newsom's Marriage

Before she was Donald Trump Jr.'s fiancée, Kimberly Guilfoyle was married to a very different political figure: California governor Gavin Newsom. Guilfoyle and Newsom met in San Francisco in the late '90s, where they both held prominent jobs. Their 2001 wedding was termed "the social event of the year," and as Newsom began pursuing a career in office circa 2003, his wholesome relationship with Guilfoyle was part of his appeal. "[Kimberly] was all sparkly and happy, very beautiful at that point," democratic donor Susie Tompkins Buell told LA Times. "It was appealing, in a way. But there was always an edge."

Maybe that "edge" was ambition, or maybe it was dissatisfaction with her current life. In 2006, Guilfoyle and Newsom announced their divorce, chalking it up to busy schedules and time apart. According to the San Francisco Chronicle, Guilfoyle was splitting her time between San Francisco and New York, where she was pursuing a career in TV. "It's no secret that they have been leading separate lives," a source told the San Francisco Chronicle. She's on one coast, he's on the other — how can you make a marriage work like that?" Newsom had also alluded to problems in the relationship. "This living on different sides of the continent has taken a huge toll personally," he said, prior to his split from Guilfoyle.

A bicoastal relationship wasn't the only problem. News later broke that Newsom had cheated on Guilfoyle with the wife of his then-campaign manager, Ruby Rippey-Tourk.

The New York Times reported that Gavin Newsom's affair with Ruby Rippey-Tourk took place while his divorce from Kimberly Guilfoyle was already underway in 2005. Ruby confessed to being sexually intimate with Newsom as part of a rehab program she was undergoing at the time. Following the admission, her then-husband Alex Tourk (and Newsom's former deputy chief of staff) resigned. Newsom called a press conference to thank Alex and wish him well, before admitting to his part in the affair. "Everything you've heard and read is true," he said. "And I am deeply sorry about that." The California governor did not mention Guilfoyle, but apologized for hurting Alex.

Guilfoyle has not spoken publicly about the ramifications of the affair, and it's unclear if she knew about it before the news broke. Regardless, she was eager to put the scandal behind her. People reported that she remarried in 2006 after the divorce was finalized, this time to furniture heir Eric Villency. The pair welcomed a son, but broke up in 2009. Currently, Guilfoyle is engaged to Donald Trump Jr., and is an outspoken advocate of right-wing politics.

Between Newsom's affair and Guilfoyle's abrupt switch from democratic leanings to the Trump administration, the two have little in common. In a 2022 interview with MSNBC, Newsom said that he and his ex no longer talk. He also evaded the question of whether or not he will be attending the Guilfoyle-Trump nuptials (via Business Insider).

Beyond Kimberly Guilfoyle, Gavin Newsom and Donald Trump Jr. have something in common: They both cheated on their ex-wives. When Trump Jr. was still married to Vanessa Haydon, he met Danity Kane singer Aubrey O'Day on Season 5 of "The Celebrity Apprentice." Per Entertainment Weekly, the two struck up a friendship through social media that later culminated in a sexual relationship. Trump Jr. and O'Day parted ways in 2012 when Haydon found out about the affair, but as O'Day told Page Six in 2022, she once thought of Trump Jr. as her "soulmate." "I love him. Love, loved, love. I'll always have love for him," she said.

Trump Jr. hasn't spoken much about the alleged romance, but former "Apprentice" contestant Omarosa Manigault Newman told People she has proof that it happened. The reality star remembered O'Day showing her personal photos that Trump Jr. had shared with her, plus "a long chain of dirty texts between them."

Unlike Trump Jr., Newsom has talked openly about his affair, both at the time it occurred and in later years. "I apologized for it. I learned an enormous amount from it," the governor told the San Francisco Chronicle in 2018. "And I am every day trying to be a champion and model [...] 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."