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Donald Trump Jr.’s Engagement Comes With a Diamond Showdown

December 18, 2025
in News, U.S. News
Donald Trump Jr.’s Engagement Comes With a Diamond Showdown

Kimberly Guilfoyle didn’t just lose Donald Trump Jr.—she also appears to have lost the ring-size contest.

President Donald Trump announced his son’s engagement to socialite Bettina Anderson on Monday during a White House holiday reception.

The celebratory moment was quickly followed by a less romantic online obsession—side-by-side comparisons of Anderson’s engagement ring and the one Trump Jr. previously gave Guilfoyle, his former fiancée.

Bettina Anderson
Bettina Anderson shows off Engagement Ring. Secallender/Instagram

Roy Albers, chief gemological officer at Worthy, analyzed photos of both rings and told the Daily Mail that Guilfoyle’s emerald-cut diamond appears to be the smaller of the two.

Her ring, Albers estimated, features a stone between six and seven carats. By contrast, Forbes reported that Anderson’s diamond clocks in at around eight carats—but with a noticeably larger cut.

Kimberly Guilfoyle
Kimberly Guilfoyle flashes ring at the 2023 Conservative Political Action Conference (CPAC). Anadolu/Anadolu Agency via Getty Images

Trump Jr. and Guilfoyle dated for six years and became engaged in 2022 before splitting last year.

To make matters worse, Albers told the Mail that Trump Jr. likely spent between $200,000 and $300,000 on Guilfoyle’s ring. Anderson’s, however, appears to have come with a much steeper price tag. The jeweler estimated her diamond could retail for anywhere between $650,000 and $800,000, depending on specifics like cut quality and clarity.

Kimberly Guilfoyle and Donald Trump Jr.
Kimberly Guilfoyle and Donald Trump Jr. broadcast from the 1st day of CPAC (Conservative Political Action Conference) Pacific Press/Pacific Press/LightRocket via Ge

Matt Harris, a certified pearl specialist and gem expert at Matt Harris Designs, echoed that assessment, telling the outlet that the price gap likely comes down to size and stone quality. While Harris took another hit at Guilfoyle, speculating that Anderson’s ring color and clarity might be “better” in comparison.

Guilfoyle still comes out ahead of Trump Jr.’s first wife, Vanessa Trump, at least in the ring-size competition. The New York Post previously reported that Vanessa Trump’s engagement ring featured a roughly four-carat emerald cut diamond valued at about $100,000—a gift Trump Jr. did not pay for himself.

Vanessa and Donald Trump Jr.
Vanessa and Donald Trump Jr. at Bailey Banks and Biddle Fine Jewelers in Short Hills, New Jersey Mychal Watts/WireImage

Despite the online debate, Anderson appears unfazed as she enters this new chapter in her life. She smiled broadly as Trump Jr. announced their engagement during the White House event and later thanked the former president, expressing excitement about joining the Trump family.

“This has really been the most unforgettable weekend of my life,” Anderson said after the announcement. “I get to marry the love of my life, and I feel like the luckiest girl in the world.”

Wedding details have not yet been announced, and the newly engaged couple appears content to savor the moment—ring comparisons and all. The engagement may mark a new chapter for Trump Jr., but the internet has made sure the old ring isn’t forgotten.

The post Donald Trump Jr.’s Engagement Comes With a Diamond Showdown appeared first on The Daily Beast.

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