EXCLUSIVE: Radar Compares Bettina Anderson's Engagement Ring to the One Don Jr. Gave to Ex Kimberly Guilfoyle — to Reveal Who Got the Bigger (and More Expensive) Diamond
Donald Trump Jr. gave eerily similar engagement rings to both Bettina Anderson and Kimberly Guilfoyle.
Dec. 31 2025, Published 4:00 p.m. ET
Donald Trump Jr.'s new fiancée, Bettina Anderson, and ex-fiancée Kimberly Guilfoyle each received massive diamond engagement rings from the president's son, and a top jeweler tells RadarOnline.com exclusively who got the more impressive bauble.
Ronnie Agami of Universal Diamonds was struck by how similar the two rings are, as they are both emerald cuts, and he tells us both stones appear to be a whopping eight carats.
Bettina Anderson's Stunning Engagement Ring Revealed
Anderson flashed her new engagement ring from Don Jr. in Christmas photos.
"Bettina’s emerald cut is slightly more square, and Kimberly’s looks longer in shape. Bettina’s is a D Flawless, so perfect as far as quality goes," he said of photos of the Palm Beach socialite debuting her stunning engagement ring at Christmas.
"Kimberly’s looks like it was pretty close to that kind of quality, so I'd say the prices or value are comparable," Agami added about the value of the two rings.
Kimberly Guilfoyle Also Sported a Huge Rock
Guilfoyle also received a massive emerald cut diamond engagement ring from Don Jr.
Agami noted about Anderson, 38, and the former Fox News host, 56, "The two women seem very different, but they happen to have similar taste in men and diamonds!" due to their eerily similar rings.
Guilfoyle got her ring from Donald Trump's eldest son, 48, in a New Year's Eve proposal in 2020, although the former prosecutor and Don Jr. didn't publicly announce their engagement at the time.
The duo began dating in April 2018, shortly after Don Jr. finalized his divorce from his ex-wife and the mother of his five children, Vanessa Trump.
Two Very Different Women
The couple showed how series they were when Don Jr. brought Anderson to the White House Easter Egg Roll in April.
Agami was right on the money about how Anderson and Guilfoyle couldn't be more different.
Well-heeled Anderson comes from money, as the daughter of entrepreneur Harry Loy Anderson Jr. and philanthropist Inger Anderson. She was raised in wealth in Palm Beach, Florida, not far from the president's beloved Mar-a-Lago estate.
The fashion influencer sports a quiet luxury style and will be marrying for the first time when she ties the knot with Don Jr.
Guilfoyle was married twice, first to then-San Francisco Mayor and current California Governor Gavin Newsom from 2001 through 2006. She quickly tied the knot for a second time, marrying furniture heir Eric Villency as soon as her divorce from Newsom was finalized.
The exes welcomed a son, Ronan, in October 2006 before divorcing in 2009. Guilfoyle went on to become a high-profile conservative personality.
Relationship Overlap?
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The couple dated for approximately one year when the president's eldest son popped the question.
Don Jr. and Anderson began spending considerable time together in Florida during the summer of 2024, when they were photographed on several lunch outings.
She made a curious appearance at the July 2024 Republican National Convention, sitting behind Don Jr. and Guilfoyle as the three watched his dad accept the party's presidential nomination. At the same event, Anderson and Vanessa were spotted happily chatting, as the two Palm Beach residents are reportedly close.
As rumors swirled throughout the fall of 2024 that Don Jr. and Guilfoyle were on the rocks, he confirmed in December of that year that the duo had split.
"Kimberly and I will never stop caring for each other and will always keep a special bond," the real estate heir revealed in a December 13, 2024, statement. One month later, he brought Anderson as his date to his dad's inauguration.
The duo shared their engagement joy with friends and family at a party thrown by his dad at the White House on December 15.
