Kimberly Guilfoyle 'Started Wearing Her Own Engagement Ring' After Don Trump Jr. 'Never Proposed,' Source Claims
Kimberly Guilfoyle is believed to have purchased her own engagement ring.
Oct. 15 2026, Published 1:30 p.m. ET
Kimberly Guilfoyle is said to have begun wearing her own engagement ring despite Donald Trump Jr. never proposing, RadarOnline can report.
Guilfoyle allegedly bought her own ring, began wearing it, and announced the engagement herself, pressuring Don Jr. to go along with the narrative, according to sources.
Kimberly Guilfoyle 'Started Wearing Her Own Engagement Ring'
Guilfoyle bought her own engagement ring because Donald Trump Jr. did not propose, according to sources.
An unnamed source told a publication that Guilfoyle "procured and started wearing her own engagement ring during the relationship" before "ultimately prompting an engagement announcement that Guilfoyle herself released."
Friends of Don Jr. reportedly had serious concerns about the relationship and were relieved when it ended.
Donald Trump Jr. Married Bettina Anderson After Split
Donald Trump Jr. eventually married Bettina Anderson after breaking up with Guilfoyle.
The relationship eventually fell apart, with Don Jr. moving on with Palm Beach socialite Bettina Anderson.
A publication published photos of the pair at the Honor Bar in Palm Beach on August 17, 2024, describing the encounter as an early public sign that Don Jr. was pursuing another relationship – Anderson kissed Don Jr. several times during the outing.
On December 10, 2024, it published additional photos of the pair walking hand in hand after dinner.
Don Jr. has since married Anderson.
Kimberly Guilfoyle Asked to Resign
Guilfoyle was asked to resign after a report accused her of using her position to make back door deals.
As Radar previously reported, President Trump has also faced questions about his relationship with Guilfoyle. The president and the former Fox News host maintained a mutually beneficial political relationship.
Guilfoyle promoted the MAGA movement through her public appearances and social media platforms, while Trump helped advance her political career.
However, that relationship reportedly came under strain following a report alleging that Guilfoyle used political donors to cover personal debts and made promises about deals tied to the president’s performance.
Trump and the White House publicly addressed the allegations, as the administration subsequently urged Guilfoyle to resign.
A Diplomatic Exit
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Guilfoyle has denied all of the allegations.
Guilfoyle’s appointment as U.S. ambassador to Greece came as Don Jr.'s relationship with Anderson was attracting public attention.
"Kimberly wasn’t sent to Greece just because of her skills," a source previously said. "It also solved a complicated personal problem. Having her thousands of miles away worked for everyone."
The claim, however, remains an allegation attributed to an unnamed source.
