Anna Osceola’s engagement ring makes it official that she is now off the market and engaged to Mad Men co-star Jon Hamm! The twosome got engaged in February 2023. The world erupted in cheers as Jon and Anna are on their way to marriage.
We got on an EXCLUSIVE phone call with Benjamin Khordipour, G.D., the author, lecturer, and GIA-certified gemologist of Estate Diamond Jewelry for a professional assessment of this lovely ring. Click here to see what he said.
Hot Details on Anna Osceola’s Engagement Ring
Jon Hamm and Anna Osceola’s engagement was private. The lovely couple is not on any social media platforms, so there was no immediate breaking news. Still, fans and the press soon got wind of Anna Osceola’s engagement ring.
Jon Hamm proposed to Anna with a simple, elegant ring featuring a 6-carat solitaire emerald cut diamond, prong-set on a thin 18k yellow gold band.
The ring made its first public debut at the 2023 Vanity Fair Oscars afterparty.
Later speaking with PEOPLE, Jon Hamm felt terrified of proposing to Anna. His parents divorced early on in life, so he “didn’t look at marriage as a thing.”
“Obviously, my parents were not married long, so I don’t have a model to look at and go, ‘Oh, this is how one finds happiness,’ ” he explained. “I just knew at a certain point I wanted to be with this person. But when I proposed, I was terrified. I was like, ‘What am I doing?’ “
Jon overcame those proposal jitters and got Anna’s elusive yes with the wonderful emerald-cut diamond ring. It is quite lovely and elegant, and easily seen from afar.
The emerald-cut diamond is one of the most popular diamond cuts on many celebrity engagement rings. Known for its hall of mirrors effect that draws you in, it also creates a large profile on the wearer’s finger with its elongated rectangular shape. Anna’s ring features a yellow gold band that creates warm, classic tones with the large diamond.
How Much Is the Ring Worth?
Our phone conversation with Benjamin Khordipour, G.D., the jewelry specialist of NYC’s Estate Diamond Jewelry who holds advanced degrees from Gübelin and the Gemological Institute of America, gave a proper, professional look at the ring. He placed its value at $400,000.
The biggest determiner of this pricing is the stunning 6-carat emerald-cut diamond. Diamonds of this quality, clarity, and weight are very rare, commanding very high prices in the industry. While second only to the solitaire diamond, that 18k gold band also adds to its total, along with its simple, impeccable craftsmanship.
Jon and Anna’s Love Story
Jon and Anna are co-stars in the AMC series Mad Men. They first met on set in 2015, filming the series’ final episode, “Person to Person,” where she plays the receptionist at Esalen, a spiritual California retreat facility where he finds peace.
Jon was there from the very beginning of the show, while Anna appeared only in the season finale and the last episode ever. However, that fateful meeting, on and off the show, sparked their romance.
However, it would take a few years for their love story to start, as Jon was still with actress Jennifer Westfeldt. They were in a long-term relationship from 1997 to 2015.
The press and paparazzi saw Jon with Jenny Slate on a movie date in New York in June 2017. They also spotted him with Lindsay Shookus at a Derren Brown: Secret Broadway premiere on September 15, 2019. On September 22, they attended the 71st Emmy Awards in LA. Then, they were also at a Saturday Night Live afterparty in New York on November 16.
However, these sightings were only casual dates.
Jon and Anna Become Unofficially Official
Press and paparazzi started spotting the couple hanging out and dating in 2020. Since they keep off social media, there were no formal announcements or hard launch of any sort. Jon and Anna sightings from here on became more regular as the press spotted them on dinner dates, played sports, went on beach trips, and took a vacation in Italy in September 2021.
They made their first red carpet appearance at the Mercedes-Benz Academy Awards viewing party and the 2022 Vanity Fair Oscar Party, both on March 27, 2022.
In 2022, the couple’s sightings at award shows and movie screenings became more steady. Apart from many public appearances, they were also at the May 2022 red carpet for the musical Bedwetter. That June, they appeared at the ESPY Awards. Then, in August, they attended the screening of their joint project Confess, Fletch, which was the second time they paired up again, this time in a movie together.
Speaking with Howard Stern on his SiriusXM show, he reflected on their relationship, stating, “This is all part of what I’m saying. This is another place in my life that I feel very settled and comfortable. I’m in a relationship right now, and it’s comfortable.”
Jon added that he’s been able to sit down to start “really thinking about all that stuff, that’s made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.”
