Kimberly Guilfoyle has been part of Trump world since 2018, when she first began dating Donald Trump Jr. following his divorce from Vanessa Haydon. Since 2016, Guilfoyle has played a role in President Donald Trump's career, from joining the pro-Trump Super PAC America First during the 2018 mid-term elections to landing her current role as ambassador to Greece (despite her breakup with Trump Jr. in 2024 ). Given her VIP status in the exclusive Trump orbit, it's no wonder Guilfoyle developed a reportedly close relationship with Charlie Kirk, another Trump ally who was shot and killed while speaking at an event on the Utah Valley University campus in September 2025.

The pair was actually so close that Guilfoyle was there to witness Charlie's pre-date jitters ahead of his first outing with

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