PRESIDENT Donald Trump’s eldest son, Donald Trump Jr., has been called out for a photo on his bookshelf displayed during a recent livestream.
Multiple outlets have reported on the photo of Don. Jr., 47, with his ex-fiancée Kimberly Guilfoyle, a 56-year-old TV personality and former prosecutor.
The photo matches a picture taken at the Ocean Reef Club in Key Largo, Florida—about an hour and 20-minute drive south of Miami— that Guilfoyle posted in April 2021.
Don Jr. wore a suit and bowtie while Guilfoyle showed off a plunge-neck pink dress as they celebrated their anniversary.
The photo caption read: “Incredible weekend @oceanreefclub celebrating our anniversary and the beautiful wedding of Robert and Carly Desmond.”
Nearly four years later, the photo sat over Don Jr.’s shoulder during a livestream for the DC Blockchain Summit 2025.
Don Jr. and Guilfoyle broke up late last year and the president’s son has a new girlfriend, Palm Beach socialite Bettina Anderson.
The Daily Beast wrote on X on Wednesday, “President Donald Trump’s son doesn’t seem to be completely over ex-fiancée Kimberly Guilfoyle.”
One X user defended Don Jr., commenting: “Just because you have pictures of people you’re no longer with doesn’t mean that you r******.”
While some Facebook users trolled Don Jr. over still having a photo of his ex on his bookshelf, his fans stuck up for him.
One Facebook user wrote: “Who the hell cares!”
“He probably didn’t even know they were there,” another wrote.
A third commented: “Poor desperate democrats.”
The U.S. Sun has reached out to Don. Jr.
DON JR. AND GUILFOYLE CALL IT QUITS
The couple called off their engagement in December 2024 after a six-year relationship.
Reports of Don Jr. and Guilfoyle dating began to circulate in April 2018, shortly after the president’s son separated from his former wife, Vanessa Trump, after 13 years of marriage and five children together.
The two announced that they were engaged in 2020.
Guilfoyle remains close with the Trump family and is even Trump’s pick for U.S. ambassador to Greece.
DON JR.’S NEW BOO
During his 47th birthday celebration at his father’s Mar-a-Lago club on December 31, Don Jr. was spotted holding hands with his new 38-year-old girlfriend.
Guilfoyle kept things cordial on social media, posting a collage of pictures of her, Don Jr. and his kids in celebration of her ex’s birthday.
Don Jr. and his new flame were seen cozying up during Trump’s joint address to Congress earlier this month.
In one photo, Anderson appeared to be poking at Don Jr.’s beard as the two smiled.
Kimberly Guilfoyle and Don Trump Jr.’s Relationship
April 2018:
Reports began circulating that Donald Trump Jr. was dating Kimberly Guilfoyle, a former prosecutor and Fox News host, shortly after Trump Jr. separated from his wife, Vanessa Trump. At this point, the couple was seen together at several events, sparking rumors about their relationship.
June 2018:
Trump Jr. and Guilfoyle made their first public appearance as a couple at a Montana rally. They attended a Fourth of July celebration together, and their relationship became more public.
July 2018:
They attended several events together, including the annual Fourth of July festivities and other Republican fundraisers. Guilfoyle also left her position at Fox News to join the pro-Trump super PAC, America First, indicating a deeper political alignment with Trump Jr. and his family.
2019-2020:
Guilfoyle became an integral part of Trump Jr.’s life, often accompanying him at rallies and Republican events. She was heavily involved in President Trump’s reelection campaign and worked as a top fundraiser. The couple became very public about their relationship, frequently sharing photos and moments on social media.
August 2020:
Kimberly Guilfoyle delivered a fiery speech at the RNC, which gained significant media attention. She continued to be a prominent supporter of Trump Jr. and the Trump family throughout the 2020 campaign.
December 2020:
Speculation began that Trump Jr. and Guilfoyle were engaged, though there was no official confirmation at the time. Reports indicated that they were serious and planning a future together.
January 6, 2021:
Both Trump Jr. and Guilfoyle were present at the rally that preceded the storming of the U.S. Capitol. Videos emerged showing them in a celebratory mood before the chaos unfolded.
2022:
It was confirmed that Donald Trump Jr. and Kimberly Guilfoyle were engaged. Guilfoyle was seen wearing an engagement ring in photos shared on social media during a New Year’s Eve celebration at Mar-a-Lago.
2024:
Guilfoyle spoke again at the RNC giving her unwavering support to her fiancé’s father, Donald Trump. Trump Jr. and Guilfoyle remain a prominent political couple, attending events together and staying active in conservative media and political fundraising efforts.
ANDERSON ‘HAPPY’ FOR DON JR.’S EX-WIFE
Don Jr. isn’t the only Trump with a new boo.
Vanessa Trump and golf pro Tiger Woods went Instagram public with their relationship on March 23 after rumors swirled about the budding romance.
Woods shared two photos of himself and Vanessa, writing, “Love is in the air and life is better with you by my side!”
Anderson sent her love to the couple, commenting on Woods’ post: “Beautiful couple. So happy for you both.”
Ivanka Trump, Don Jr.’s sister, also said she was happy for the couple.
