With the announcement of Donald Trump Jr.’s engagement to Palm Beach socialite Bettina Anderson, many are now comparing this new chapter to his 2020 engagement to Kimberly Guilfoyle.
Don Jr. and Anderson confirmed their engagement following news shared by President Trump at a White House holiday party on Monday, December 15, marking a fresh start after his 2024 split from Guilfoyle. The model looked radiant in a strapless red dress and showed off her bling as she took to the podium to thank the crowd.
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Experts Compare Bettina Anderson's Engagement Ring to Kimberly Guilfoyle's
Naturally, experts were brought in to compare the differences between the two engagement rings and weigh in on which might be more impressive. Forbes reported that Bettina’s ring features an exceptional 8-carat D-color flawless emerald-cut diamond, certified by the Gemological Institute of America (GIA), flanked by two half-carat shield-cut diamonds.
For the proposal, Trump Jr. enlisted renowned jeweler and artist Sue Gragg, who shared insights with the outlet about the creation process.
“Of all the celebrity engagement rings—and engagement rings in general—this is for sure my favorite,” Gragg said in the interview. “I’m honored to have made it. I’m honored that he called me, and I'm honored that I made that ring to go on her precious hand.”
As for Guilfoyle, Roy Albers, Chief Gemological Officer at Worthy, told the Daily Mail, “Kimberly Guilfoyle's engagement ring features an emerald-cut diamond estimated to be between six and seven carats.” He added, “The amount he paid was likely between $200,000 and $300,000 depending on the quality of the diamond. On the other hand, Bettina's ring is believed to retail between approximately $650,000 and $800,000.”
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Matt Harris, certified pearl specialist and gem expert at Matt Harris Designs, noted that one of the biggest differences between the rings is their size. “It's also a safe bet to assume the color and clarity of Bettina's ring might be ‘better,’” Harris shared with the Daily Mail.
Don Jr. and Guilfoyle began dating in 2018 following his divorce from Vanessa Trump, who is now engaged to Tiger Woods. Their relationship reportedly ended quietly around the last election, with sources suggesting that Don Jr. initiated the split. In late 2024, Guilfoyle was appointed U.S. Ambassador to Greece by Donald Trump.
Meanwhile, the businessman and Bettina were publicly linked later in 2024, with their relationship confirmed through joint appearances at high-profile events, including the January 2025 inauguration.
Anderson, a Palm Beach socialite and model, is the daughter of philanthropist Harry Loy Anderson Jr. and grew up in a prominent family.
