Kimberly Guilfoyle Not Getting Along With Don Jr.’s Daughter Kai Trump is Just Hard to Ignore

The dynamics within blended families can be complicated, and the Trump family is no exception. Recent events have highlighted tension between Donald Trump Jr.’s fiancée, Kimberly Guilfoyle, and his oldest daughter, Kai Trump. The tension became particularly evident during the recent election celebrations at Mar-a-Lago.

The 17-year-old Kai provided a glimpse behind the scenes on election night in a particularly memorable moment on her personal vlog. What stood out was how the video completely excluded Guilfoyle from the family photos. “We have to get Elon with his boy. Gorgeous perfect boy,” Donald Trump was heard saying as he arranged what Kai later referred to as ‘the whole squad’ photo. Elon Musk and his son X Æ A-12 were also present, but Guilfoyle was not. Instead, Kai’s mother, Vanessa Trump, appeared beside her ex-husband and their children, looking thrilled.

The social media landscape tells an equally revealing story. A quick look at Instagram shows that while Guilfoyle follows her potential stepdaughter, Kai does not follow her back. Given Kai’s growing influence within the Trump family, this digital cold shoulder speaks volumes. The election night celebrations were about more than just the arrangement of photos. Don Jr. appeared to draw away from Guilfoyle on stage as if he wanted some space, and there was a lot of side-eye going on. The Daily Beast noted that Guilfoyle may have been the only woman in the world more somber than Vice President Kamala Harris following Tuesday’s election results—and all the contouring in the world couldn’t hide it on her face.

The timing of these snubs aligns with swirling rumors about Don Jr.’s alleged relationship with Palm Beach socialite Bettina Anderson. Anderson has already developed a tight relationship with Kai and Vanessa. Over the summer, she was spotted hanging out with them at several laid-back get-togethers. “Kimberly either didn’t know about Bettina — or didn’t want to know,” an insider revealed to The Daily Mail .

Details of Don Jr.’s alleged involvement with Anderson emerged in September, painting a picture of a very public “open secret” in Palm Beach’s elite Republican circles. Witnesses noticed a very telling moment inside Palm Beach’s Honor Bar. The two were seen enjoying a cozy lunch together. “She seemed totally smitten with Don – and he with her,” a source revealed, noting Anderson’s casual yet striking appearance in “a white shirt tied off to show her midriff and wide-leg pants.” The source added that while “they weren’t exactly making out, but the kisses were romantic, and you could tell they were intimate with each other,” as per Ok! Magazine .

For Guilfoyle, these signs of discord with Kai could spell trouble for her future in the Trump inner circle. Kai has emerged as a powerful voice in her grandfather’s political movement, especially after her impressive speech at the Republican National Convention. Her ability to “humanize” her “normal grandpa” and connect with young voters has made her an increasingly important figure in the family’s political narrative.