Jon Hamm’s Fiancee Anna Osceola Shows Off Stunning Engagement Ring In Rare Photos

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Jon Hamm‘s fiancée is sporting a gorgeous rock on her finger! Anna Osceola, 34, showed off her engagement ring when the couple stepped out in New York City on Wednesday, May 10. Anna got engaged to the 52-year-old Mad Men star earlier this year, but this was the first time that she appeared in public while wearing her engagement ring. Jon definitely did not disappoint with the ring he picked out for his future wife!

Jon and Anna walked side-by-side on the busy streets of NYC on the sunny day. Jon wore a blue jacket over a white T-shirt with blue jeans, a brown belt, and white Adidas sneakers. The Emmy Award winner also wore a pair of brown sunglasses and a yellow hat. Anna wore a light-blue button up shirt, over a white shirt that she tucked into a pair of matching jeans. The future Mrs. Jon Hamm rounded out her look with a green cross-body purse, aviator sunglasses, and white sneakers. But it was Anna’s engagement ring that really stood out from the photos of the couple.

News of Jon and Anna’s engagement broke on February 26 via People, though neither star confirmed the engagement themselves. The duo first met back in 2015, when Anna appeared on the series finale of Mad Men. And in an interview back in 2022, the Top Gun: Maverick actor admitted to being serious about her. “I’m in a relationship right now and … it’s comfortable, it’s a feeling of taking care of someone else and being taken care of,” he said in September on an episode of The Howard Stern Show.

Prior to their engagement, Jon and Anna enjoyed a number of romantic outings together, including a getaway to Italy in September of 2021. The couple made their red-carpet debut at the Oscars in March of 2022. Once they say “I do,” Anna will be Jon’s first wife. He was previously in a nearly two-decade-long relationship with actress Jennifer Westfeldt from 1997 to 2015, but they never married.