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Jon Hamm proposed with a $350k ring that's out of this world

Jon famously once said he would never marry

Faye James
Senior Editor
June 27, 2023
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Mad Men co-stars Jon Hamm and Anna Osceola surprised fans this weekend as they said their vows in an intimate wedding ceremony at Big Sur - an iconic location made famous by the TV series' finale in 2015. 

The couple first crossed paths on the set of Mad Men in 2015 as co-stars, eventually making their relationship official in 2020, and announcing their engagement earlier this year in February.

While fans eagerly anticipate glimpses of the couple's nuptial bands, diamond specialists at UK's celebrated retailer Steven Stone have given us a sneak peek into Anna's stunning engagement ring. 

Jon proposed with an outstanding 6ct emerald cut diamond ring that is believed to be worth a jaw-dropping $350,000. 

Jon Hamm and Anna Osceola attend the 2022 Vanity Fair Oscar Party hosted by Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 27, 2022 in Beverly Hills, California© Getty
Jon Hamm and Anna Osceola attend the 2022 Vanity Fair Oscar Party hosted by Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 27, 2022 in Beverly Hills, California

"Emanating a timeless charm traced back to the 1500s, emerald cut diamonds beautifully radiate sophistication and effortless style. Known to symbolise an open heart and personal clarity, they are an increasingly popular choice for engagement rings among celebrities," explained Maxwell Stone, Diamond Expert at Steven Stone.

Emerald-cut gems have indeed found their way into the engagement rings of numerous celebrities this year, including those gracing the fingers of Stranger Things star Millie Bobby Brown and actress Bella Thorne.

MORE: Jon Hamm makes rare statement about his future with girlfriend Anna Osceola

Millie Brown's engagement ring has the same cut as the one Jon bought for Anna© Instagram
Millie Brown's engagement ring has the same cut as the one Jon bought for Anna

Resting majestically on a yellow gold band, the colossal diamond adorns a classic solitaire setting, cleverly drawing attention to the spectacular centrepiece. 

Maxwell added: "A solitaire setting is a timeless choice, offering excellent support and matching beautifully with any diamond shape. Anna's glittering gem is estimated to be worth an impressive $350,000."

The celebrity-studded nuptials were first reported by TMZ, who noted the guest list featured famous faces like Billy Crudup, Paul Rudd, and Tina Fey. Adding a dash of cinematic nostalgia, the couple chose the 1967 James Bond film's theme You Only Live Twice as their walkup song.

Anna Osceola, Jon Hamm attend the 2023 Vanity Fair Oscar Party Hosted By Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 12, 2023 in Beverly Hills, California© Getty
Anna Osceola, Jon Hamm attend the 2023 Vanity Fair Oscar Party Hosted By Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 12, 2023 in Beverly Hills, California

While the duo has always been reticent about their relationship, they have made a handful of red-carpet appearances together and starred in the 2022 crime flick Confess, Fletch.

Jon, however, offered a rare insight into his love life during a candid interview with Howard Stern in September 2022, opening up about his struggle with trauma and its impact on his ability to commit. 

Tina Fey and Jon Hamm © Frazer Harrison
Tina Fey and Jon Hamm

"Yes. I've never been married, but I could for sure," he responded when asked about the prospect of marriage. He elaborated, "This is another place in my life that I feel very settled and comfortable with. I'm in a relationship now and it's comfortable, it's a feeling… Taking care of someone else and being taken care of."

Describing his journey towards self-improvement and mental wellness, he revealed: "It has also been a process of working on myself, my mental health, all this stuff with my therapist and unpacking all of that trauma," and admitted how early traumas had previously hindered his emotional availability. 

Jon Hamm and Tina Fey star in Maggie Moore(s)

He added: "It has made the relationship I'm in now more meaningful, and opened up the possibility of being married, having kids, defining a new version of happiness, life, wellness…"

Prior to his romance with Anna, Jon shared an 18-year long relationship with Jennifer Westfedt from 1997 to 2015.

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