Don Jr. has proposed to socialite Bettina Anderson, marking his second engagement in five years. He was previously set to marry diplomat Kimberly Guilfoyle, but the relationship did not work out, and they broke up in 2024.
Nevertheless, Don Jr. certainly knows how to keep his lady love happy by gifting her the choicest of diamonds. Both Anderson and Guilfoyle received massive gemstones on their engagements. Given how close the two proposals were, comparisons between their rings are inevitable.
A comparison of the two rings shows a clear winner. Anderson’s ring became the talk of the town after she flaunted the stone on her left hand during the White House Christmas party. According to Forbes, the ring features an exquisite 8-carat.
Bettina Anderson showcases her 8-carat emerald-cut diamond engagement ring from Donald Trump Jr. at a White House event. The flawless D-color gem, designed by Sue Gragg.#bettinaanderson #donaldtrumpjr #engagement #ring #diamond pic.twitter.com/LdFJhxG5mc
— Heading (@HeadingDaily) December 17, 2025
The D-color flawless stone has been designed by Sue Gragg and has earned certification from the Gemological Institute of America. Apart from the 8-carat main diamond, the ring also features two half-karat shield-cut diamonds. The cost, you ask? A whopping $650,000 to $800,000.
This is what gemstone expert Roy Albers revealed in an interview with the Daily Mail. He said, “Bettina’s ring is believed to retail between approximately $650,000 and $800,000.” Now let’s compare it to Guilfoyle’s engagement ring, which she proudly wore after making her relationship with Don Jr. official in 2022.
Interestingly, Guilfoyle also received an emerald-cut diamond. But the weight and worth of the ring are significantly less than that of Anderson’s. It looks like Don Jr. has upped his game when it comes to jewelry over the years, as some industry experts believe Guilfoyle’s ring weighed around 5 carats and carried a price tag of $65,000 to $125,000.
However, Albers’ opinion slightly differs. According to him, the diamond in question is between six and seven carats, and the ring could have cost anything between $200,000 and $300,000. He revealed, “Kimberly Guilfoyle’s engagement ring features an emerald cut diamond estimated to be between six and seven carats. The amount he paid was likely between $200,000 and $300,000, depending on the quality of the diamond.”
Did he give her Kimberly’s ring? She also was given an 8ct emerald cut ring. pic.twitter.com/7eh6MDv6qc
— Mickie (@GriffinTheory) December 18, 2025
Hence, different experts have different views on Guilfoyle’s ring, but one thing is clear: Anderson’s diamond is superior to hers. Certified Pearl Specialist Matt Harris echoed similar thoughts in a statement to the Daily Mail. He stated, “It’s also a safe bet to assume the color and clarity of Bettina’s ring might be ‘better’. Flawless diamonds are hard to come by and usually not chosen for a first engagement.”
At least on the diamond front, Anderson got the upgrade. The 39-year-old socialite from Palm Beach was rumored to be dating Don Jr. for months before Donald Trump announced their engagement during the White House Christmas party on December 15.
On the other hand, Guilfoyle is currently busy with her diplomatic assignments as she serves as the US ambassador to Greece. The former prosecutor reportedly got engaged to Don Jr. in 2020, but the couple kept their relationship private until 2022. Two years later, they announced their split in 2024.
