A lot of details have come to light since Kimberly Guilfoyle and Donald Trump Jr. secretly called off their wedding. Although breakup rumors had been swirling for months, Guilfoyle and Don Jr. didn’t confirm the news until the end of 2024, following reports linking him to socialite Bettina Anderson. “Don and Kimberly broke up before the election and started to divide assets around the end of September,” a source told Us Weekly that December, noting it was the first son who ultimately called things off between him and Guilfoyle. The insider also stressed that the split was “amicable” and explained the reasoning behind their decision. “They just had different goals,” according to the insider.

However, a separate report claims there might be some overlap involved. At the time news of their breakup surfaced, an insider alleged that Don Jr. and Anderson had been secretly dating for six months already and that Guilfoyle knew of the relationship but chose to turn a blind eye. “She loves the power and lifestyle,” the insider dished, per People. Meanwhile, Junior made no secret of his affair with Anderson and would even take her to trips around the country. “Don is smitten with her,” the source said of the new couple. “Who knows what, if anything, will come from this.”

After being engaged for four years, Don Jr. confirmed that he and Guilfoyle had quietly parted ways in a vague but telling statement released to Page Six. He sent her well-wishes while congratulating the former Fox News anchor for being appointed the U.S. ambassador to Greece. However, red flags suggest that Guilfoyle and Don Jr.’s breakup was far messier than the two let on. 

In the wake of their split, sources claim that Kimberly Guilfoyle’s gaudy style and party girl ways flushed her engagement to Donald Trump Jr. down the drain. An insider told the Daily Mail that she had earned the nickname “Margarita girl” thanks to her love of drinks and partying. “She’s also amazingly ambitious,” another insider stressed. “Don Jr. is a smart guy and very right wing, but he’s not so bothered about power. … But for Kimberly, it’s about power, power, power!” 

Speaking of freedom, the eldest son of Donald Trump reportedly also believed Guilfoyle could be a little overbearing. Even her fashion choices had led to arguments between the former couple, with Don Jr. frequently griping about his then-fiancee’s wardrobe. “Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels, and never looks relaxed or casual,” an insider told People. (To be fair, he’s not exaggerating; Guilfoyle has a terrible habit of confusing charity events for the nightclub and is very rarely seen in unostentatious ensembles.) “The tight dresses need to go and she has been told that.”

In fact, Guilfoyle’s inappropriate outfits reportedly landed her on Donald Trump’s bad list, which sources say contributed to Don Jr. calling off their engagement. “Don Jr. has always wanted to look good in his father’s eyes,” the People source noted. “Someone like Bettina [Anderson], who is and has been a model, and is in Waspy circles of Palm Beach, is something that [Don Jr. knew] would impress him.” (See also: Don Jr.’s PDA pics with his mistress-turned-girlfriend are the biggest gut-punch to Guilfoyle.)