Don Jr. reveals photos of an old flame on his shelf during livestream
Donald Trump Jr. revealed Wednesday he still has an old photo of he and his former fiancee Kimberly Guilfoyle on his bookshelf.
The framed photo of Guilfoyle, 59, was spotted on a shelf behind Trump Jr. sitting on the shelf over his shoulder as he live-streamed into a panel at the DC Blockchain Summit 2025.
The photo matches an image of the pair posted from the Ocean Reef Club on Guilfoyle’s Instagram account in 2021.
Trump Jr. and Guilfoyle started dating in 2018 and got engaged in 2020 but ended their relationship in December 2024.
Guilfoyle and Don Jr were pictured for a last time together on November 14, when she posted photos from a Trump victory celebration at Mar-a-Lago.
As DailyMail.com exclusively reported in December, Trump Jr. and Guilfoyle called off the engagement as the Trump heir was spotted publicly with Palm Beach socialite Bettina Anderson.
In December, Trump nominated Guilfoyle to the next ambassador of Greece.
She has yet to receive Senate confirmation for the ambassadorship
Donald Trump Jr. streams from the DC Blockchain Summit
An old 2021 photo of Donald Trump Jr. and Kimberly Guilfoyle posted on Instagram
During the cryptocurrency summit, Trump Jr. spoke about his interest in cryptocurrency that he said developed after his father became president of the United States.
He said it was increasingly difficult to get loans approved, after his father became president, citing the ‘discriminatory’ and ‘inefficient’ the normal banking and market system was.
Although Guilfoyle is less-frequently spotted at Trump Jr.’s side, she continues to appear in the Trump family orbit.
Guilfoyle appeared on Tuesday at 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,’ Trump said at the reception.
Guilfoyle 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.
Over the weekend, Guilfoyle also made a public appearance to attend the Wags to Riches Gala at the president’s club at Mar-a-Lago, a fundraiser for animal welfare and rescue efforts.
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