Trump Can’t Stand Don Jr.’s 'Annoying' Fiancée Kimberly Guilfoyle Because of Another Child: Source

Donald Trump’s apparent distaste for his son’s fiancée, Kimberly Guilfoyle, has posed more than a few eyebrows. Known for her prominent role as a conservative fundraiser and media personality, Guilfoyle’s relationship with Donald Trump Jr. might seem like a natural alliance given her alignment with Trump family politics. However, rumors suggest that the elder Donald's disapproval stems from a deeply rooted preference for his daughter Ivanka Trump, casting a shadow over his acceptance of Guilfoyle.

Sources suggest that Donald's discontent escalated in 2019, after Guilfoyle allegedly stole attention from Ivanka and her husband, Jared Kushner, during a Fourth of July event. This led Trump to push back against Guilfoyle’s presence at subsequent family gatherings, even wanting her absent from Thanksgiving celebrations so that Ivanka could remain in the spotlight. The White House, at the time, dismissed these claims as false, but the whispers persisted.

In 2021, sources claimed that Donald found Guilfoyle’s presence ‘annoying,’ a label he has never publicly used for Ivanka. This perception likely set the tone for her interactions with the Trump family, making it difficult for her to integrate fully. While Ivanka has consistently held a unique position, Guilfoyle’s enthusiastic embrace of the Trump brand has not won her the same favor. Fischer claimed, "When he is talking about Ivanka versus any of his other children, it's just night and day. There is a softness, a gentleness, humane aspect to Donald Trump that we never see under any other conditions."

From early on, it was clear that Ivanka held a special place in the president-elect's heart and career. He frequently praised her, often in ways that raised eyebrows. Over the years, Donald made unsettling remarks about Ivanka’s appearance and their relationship, even hinting at a hypothetical dating scenario on The View in 2006. Trump had said, “I’ve said if Ivanka weren’t my daughter, perhaps I’d be dating her.”

According to journalist Marc Fisher, Trump’s dynamic with Ivanka is noticeably softer than with any of his other children, whom he apparently pushes to compete against one another while keeping Ivanka on a pedestal. Moreover, In 2015, Trump gushed, “Yeah, she’s really something, and what a beauty, that one. If I weren’t happily married and, ya know, her father…” as reported by Irish Star. 

This deep-seated favoritism may explain Trump’s aversion to Guilfoyle, who has seemed to pull focus from Ivanka in ways her father resents. Since 2018, when Donald Jr. and Guilfoyle began dating, the GOP leader has reportedly taken issue with her influence within his inner circle.

As per Daily Beast, Guilfoyle often appears as an outsider, evidenced by moments like the celebration in Palm Beach where she was conspicuously excluded from family pictures and was even avoided by Donald Jr. on stage. To further complicate matters, recent rumors surrounding Donald Jr. add tension to the situation. Reports of him spending time with Palm Beach socialite Bettina Anderson surfaced this September, with sources claiming, “They’re not trying to hide it. They’ve been seen together all over Palm Beach.” Although neither Donald Jr. nor Guilfoyle commented on these claims, the strain seemed visible during their campaign appearances, where they appeared distant and tense.