Signs Don Jr. Is Kimberly Guilfoyle's Least Favorite Ex

Kimberly Guilfoyle plays two important roles in the Trump administration; first, as the U.S. ambassador to Greece, and the second as a person who isn't bothered by how quickly her ex-fiancé moved on. While the former Fox News anchor has tried her best to make it seem like she and Don Jr. ended on good terms, Guilfoyle reportedly can't keep the act up behind the scenes. In December 2025, a confidant disclosed to the Daily Mail that the news of Don Jr. and Bettina Anderson's engagement had put a dampener on Guilfoyle's festive cheer. 

"Kim is agitated by Bettina," they shared. "She has been ill-tempered the past few days. She yells at meetings. She came late to a Christmas party and barely stayed. Not the usual social butterfly that she usually is." According to one source, the Trump staffer urged her inner circle to refer to Anderson only by a demeaning moniker she'd bestowed upon her, rather than by name. While Guilfoyle's rumored meltdown over Don Jr.'s engagement tore her amicable exes act to shreds, it wasn't the only sign things weren't as rosy as they seemed. 

When the former Fox News host spoke to ANT1, in November 2025, Guilfoyle confirmed that she was on good terms with both of her ex-husbands, California Governor Gavin Newsom and Eric Villency. The blatant omission of Don Jr. only seems more eyebrow-raising when we consider that she shouted out Newsom, who not only has vastly different political views but has also admitted to cheating on her. In fact, when we compare how Guilfoyle has spoken about her exes through the years, her dislike for Don Jr. is blatant.

Kimberly Guilfoyle's relationship with her second ex-husband, Eric Villency, seems to be in a pretty great place nowadays. During a 2015 interview with Mediaite, the author opened up about her strong bond with the father of her only child. "Even though we're divorced, I'm still very close with his family," Guilfoyle gushed. "Even when people don't stay married, they can still be a family together. That's been something that's been really good for developing me as a person." The Trump staffer has backed that statement up with her actions, sharing a bunch of photos of them from family hangouts.

Notably, Guilfoyle also reconnected with Gavin Newsom following her split from Donald Trump Jr. After the late Charlie Kirk appeared on the California governor's eponymous podcast, in March 2025, people were naturally left wondering how their paths could have possibly crossed in the first place. Kirk laid the doubts to rest shortly afterward, telling Fox 11 that Guilfoyle, who was also a friend of his, had helped them to connect. While she has publicly maintained that everything's swell with Don Jr., Guilfoyle reportedly uttered three words about him that would deliver a blow to his Trump-like ego. 

According to a Daily Mail insider, behind closed doors, she snarked about her ex-fiancé, "He's no prize." Moreover, Guilfoyle's public confession about being "loyal" hinted that the rumors that Bettina Anderson started out as Don Jr.'s mistress were a brutal blow. Given all of this, it seems that the U.S. ambassador to Greece might just be putting on a show of amicability to keep her position in the Trump administration secure.