Donald Trump Jr. Called Out by Fans for Displaying Photo of Ex-Fiancee Kimberly Guilfoyle During Livestream

Fans tuning in to a speech by Donald Trump Jr. were taken aback when they noticed a framed photo of his former fiancée Kimberly Guilfoyle on his bookshelf.

The incident occurred during his participation in a panel at the DC Blockchain Summit 2025, which was livestreamed. The framed picture of Guilfoyle, 59, was strategically placed behind Trump Jr. as he addressed the audience.

The photo of Guilfoyle on Trump Jr.'s bookshelf corresponds to an image previously shared by the former Fox News host on her Instagram account during their time at the Ocean Reef Club in 2021.

Fans pointed out the photo during the summit's livestream with several comments in the live chat asking, "Is Kimberly back in the game?"

Another said: "OMG," while a third added, "Do you see what I see?"

Trump and Guilfoyle's relationship, which began in 2018 and culminated in an engagement in 2020, came to an end in December 2024.

Their last public appearance together was on November 14 at a Trump victory celebration held at Mar-a-Lago, but they were officially broken up in December 2024 when Trump Jr. was spotted with Palm Beach socialite Bettina Anderson.

A source claimed that Trump Jr. and Anderson were seeing each other for six months before going public with their relationship, claiming that Guilfoyle "looked the other way."

Suspicions were also raised when Don Jr.’s daughter Kai Trump posted a photo of "the whole squad" in November, which included the entire Trump family (minus Melania Trump) and Elon Musk, but noticeably not Kimberly.

Following the split, President Donald Trump nominated Kimberly as the next ambassador of Greece in December, indicating a continued professional connection between the two. However, she has yet to receive Senate confirmation for the ambassadorship.

Despite their personal relationship coming to an end, the conservative commentator remains intertwined with the Trump family, as seen through her recent appearances at events such as a White House reception celebrating Greek Independence Day.

"She's really a good person, she represents the Greek culture very well, that I will tell you," Donald said at the reception.

Kimberly made remarks thanking the president, describing her new position as "the honor and privilege of a lifetime."

"I know the measure of the man and his character and his strength, and I know his love for the people of Greece, the birthplace of democracy," she continued.

Before dating Don Jr., Kimberly was married to Governor of California Gavin Newsom for five years, but the couple divorced in 2009.