California Governor Gavin Newsom and Kimberly Guilfoyle’s marriage, a union that lasted roughly three years, ended long before Guilfoyle’s relationship with Donald Trump Jr. In his memoir, “Young Man in a Hurry: A Memoir of Discovery”—which many speculate could be a step toward a 2028 presidential campaign—Newsom candidly discusses the early signs of trouble in their relationship. A pivotal moment for him came during his early days as San Francisco mayor in 2004 when he boldly challenged both state and federal laws to permit same-sex marriages. “I saw something in those marriages that I did not see in my own,” he reflected.

During San Francisco’s famed “winter of love,” numerous couples, including several of Newsom’s aides and celebrities like Rosie O’Donnell and Kelli Carpenter, who have since parted ways, wed. Newsom attributes much of his relationship’s breakdown to their diverging career paths. “Just three days after my mayoral inauguration, Kimberly headed to New York to start her new role at Court TV,” he recalled. Her career trajectory eventually led her to Fox News and into conservative political circles, a stark contrast to their shared liberal upbringing in San Francisco. Even early on, Newsom’s family sensed potential discord. His sister Hilary harbored doubts but kept them private until much later. “She was smart, very smart, but not my type of gal,” Hilary is quoted in the memoir. “She was a bit too much—always perfectly put together, but subtlety was not her strong suit.”

Today, Guilfoyle is often cited as a prime example of the “Mar-a-Lago face” trend, characterized by dramatic makeup, voluminous hair, and visible cosmetic enhancements. “She needed to command a room, to own it. She demanded attention,” Hilary further commented, noting that “her need for affection and admiration was insatiable.” At the couple’s December 2001 wedding, which took place at St. Ignatius Church followed by a reception at the Getty mansion, Newsom’s mother, Tessa, maintained a supportive facade. His father, William, was closely tied to the Getty family as a trust administrator. “My mother believed that my marriage to Kimberly wouldn’t last, but she kept those feelings from me,” Newsom wrote. However, Tessa did express her concerns to Guilfoyle. Recalling a family incident, Newsom noted that Guilfoyle wasn’t present when his mother, at just 55, opted for doctor-assisted suicide in 2002 after battling aggressive metastatic breast cancer. “Kimberly had visited the day before, only to be admonished by my mother about issues in our marriage. Kimberly left in tears,” he recounted. “It seemed my mom had finally found her voice.”

But even Newsom’s family didn’t believe the relationship problems were one-sided. ‘I saw a lot of adoration from her to you, Gavin. But less from you to her,’ Newsom’s sister Hilary pointed out. His mother, he wrote, ‘was worried that I had brought a kind of passivity into the relationship, a “go along to get along,” that was itself a devil’s bargain.’ He said that tendency is what led to the embarrassing 2004 Harper’s Bizarre photo shoot where he and Guilfoyle were sprawled out on a rug in formalwear at the Getty mansion, where they were labeled the ‘new Kennedys.’ ‘I gave only a little of myself to Kimberly. Instead of regretting this, I kept wishing I could have given a lot more to my dying mother,’ Newsom wrote.

‘The fairy tale of the new Kennedys was not to be. The distance between Kimberly and me became a breach, and the breach widened into a chasm that could not be repaired,’ he continued. ‘When it was time to part after four years of marriage, we parted about as amicably as two people could,’ he said. They announced their divorce in January 2005. Guilfoyle dated Trump Jr from 2018 to 2024, and the couple was eventually engaged.

President Donald Trump named Guilfoyle ambassador to Greece as news of Trump Jr’s new relationship with Palm Beach socialite Bettina Anderson was becoming public. Trump Jr and Anderson are now set to be wed. After a bout of bachelorhood, which Newsom admits he ‘did not handle with discernment,’ he married Jennifer Siebel Newsom, an actress and documentary film director, in 2008, and the couple has four children.