‘Mad Men’ Star Jon Hamm & Anna Osceola Are Engaged After Two Years Of Dating

Jon Hamm and Anna Osceola are engaged.

The spouses-to-be first met on the AMC series Mad Men in 2015. They were then spotted together on several occasions before rumors started about their relationship in 2020. 

Osceola first met Ham when she played a small role playing a receptionist in the series’ final episode. At the time Hamm was in a long-term relationship with Jennifer Westfeldt before splitting months later after 18 years together. 

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The couple has been seen together eating meals, playing tennis, and having romantic beach days. They made their red carpet debut in March 2022 at an Oscars afterparty. Hamm discussed his relationship with Osceola in a September 2022 interview with Howard Stern where he revealed that he could see himself being married eventually. 

“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,” he said, later adding 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.”

“It sounds hokey and whatever, but it’s real and for one of a better word, it’s what I’m working for. What else is there other than that?” he added before confirming that he is “very much so” in love.