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Kimberly Guilfoyle might have let something slip when she made a shocking confession about her past. The former Fox News host turned political operative recently landed an ambassadorship to Greece from Donald Trump — around the same time her engagement to his son, Donald Trump Jr., ended and he moved on with someone new. Now settling into her diplomatic role, Guilfoyle sat down with Greek Prime Minister Kyriakos Mitsotakis where she delivered a line that sent social media sleuths spiraling into detective mode. ‘You Got to be Real Desperate to Fall for a Trump?’: Donald Trump Jr.’s Steamy Photos with New Girlfriend Raise Eyebrows as Critics Say He’s Trying to Compete with Ex-Wife Vanessa and Tiger Woods When asked about visiting Greece before her ambassadorship, Guilfoyle got nostalgic about her 2004 honeymoon with then-husband Gavin Newsom. She’d covered the Olympic Games for ABC News that year and squeezed in what she described as their “fabulous honeymoon.” Then came the kicker that launched a thousand tweets: when asked about the marriage itself, she replied, “We’ll work on getting a new husband.” Yahoo Entertainment readers wasted no time weighing in on the revelation. “She actually looked normal when she was with Newsom,” one wrote, while another noted, “She’s an ex for a reason.” Taking a jab at both her past relationships, one person said, “Basically, Gavin upgraded with his current wife and Kimberly downgraded with Don Jr.” The observations highlighted just how much had changed since her San Francisco days, both in appearance and circumstance. The comment about finding a new husband sparked immediate speculation. “She’s been with Newsom and Trump Jr, who would want to get anywhere near that?” one person questioned, capturing the bewilderment many felt about her romantic history. Another stated the obvious on everyone’s mind: “She’s been with Newsom and Trump Jr.” Though others prefer she keep her past on the hush, hush. “It’s pretty sad when this woman can’t stop talking about her ex-husband to point out who she was, back in the day. Knock it off,” one person warned her. The reactions ranged from confused to entertained, with readers clearly invested in unpacking the layers of this situation. The backstory makes the whole situation even more complex. According to Newsweek, Guilfoyle and Newsom were San Francisco’s golden couple back in 2001, tying the knot when she worked in the district attorney’s office and he served on the board of supervisors. She demonstrated serious commitment to him by leaving her prosecutor position in 2003 to support his mayoral campaign, the kind of sacrifice that made their 2005 separation all the more surprising. By February 2006, their divorce was finalized, and she seemed to flip her political script. Guilfoyle eventually landed in Donald Trump Jr.’s orbit years later, becoming a fixture at rallies and campaign events for the Trump family. She seemed fully embedded in that world, championing causes and standing beside Don Jr. through multiple election cycles. But that relationship fell apart, too, with the eldest first son moving on with socialite Bettina Anderson while Guilfoyle received her ambassadorship earlier this year after their engagement ended. The timeline has raised eyebrows, especially since, as recently as April — right after she landed her new European post — Newsom, her ex and political opposite to her new MAGA circle, reportedly asked Guilfoyle to help with his rebranding. The gesture suggested they still shared a level of mutual respect and maintained some kind of professional connection despite their complicated history, according to People. But it was the parallel between one of Guilfoyle’s comments at the 2020 Republican National Convention and something Newsom said this week that really got people talking. During his victory speech on Tuesday, Nov. 4, after the passage of Proposition 50, Newsom echoed a line once delivered by his ex-wife on the convention stage. It’s unclear if he did it intentionally, but the moment suggested she might still be on his mind — if not romantically, then at least symbolically. “Did I, I swear to God, just hear Gavin Newsom say, ‘the best is yet to come’? His ex-wife’s tagline at the Republican convention? what a hoot,” one person tweeted. It is true the governor copied the line, despite it being a very common phrase. The final Yahoo! Entertainment comment summed up what many were thinking: “He slayed Trump and his ex,” one user wrote, pointing to how Newsom’s line seemed to hit two targets at once. Meanwhile, as Guilfoyle steps into her new role representing the U.S. in the same country where she honeymooned with Newsom nearly 20 years ago, social media is still buzzing. Whether it was a coincidence or timing, one thing’s certain: The ambassador is back in the spotlight, and it’s not because of her work.
