Jon Hamm Reportedly Engaged to Mad Men Co-Star Anna Osceola

By Kofi Outlaw

Actor Jon Hamm (51) is reportedly engaged to his longtime girlfriend, actress Anna Osceola (34). Both Hamm and Osceola are known for being very private, keeping their respective lives off of social media; however, PEOPLE has confirmed through its sources that Hamm did pop the question to Osceola. 

Jon Hamm and Anna Osceola first met on the set of Hamm's hit TV series Mad Men – specifically when filming the series finale of the show in 2015. Osceola played the desk receptionist at a cultish California retreat called Esalen, where Hamm's ad man Don Draper goes to clear his head – only to stumble on the next great capitalist idea.

It wouldn't be until years later, after Mad Men (and after Hamm ended his longtime relationship with actress/filmmaker Jennifer Westfeldt) that Hamm and Osceola would start to be seen in public together. A photo of the pair was shot in 2017, and by 2020 Hamm and Osceola were seen together on multiple occasions, sparking rumors that they were dating. Hamm and Osceola made their relationship official in public in March 2022 at an Oscars afterparty and stepped out for numerous public events that year, including the ESPY Awards and a  screening of Hamm's film Confess, Fletch, which Osceola also made an appearance in. 

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(Photo: AMC)

The big eyebrow-raising issue here is the fact that Jon Hamm is finally seeming to step into the arena of marriage. Hamm and Westfeldt were together from 1997 to 2015, without ever officially getting married. In one 2008 interview, Jon Hamm explained his and Westfeldt's arrangement in the following terms: 

"We may not have a piece of paper that says we're husband and wife, but after 10 years, Jennifer is more than just a girlfriend. What we have is much deeper and we both know that. To me, people get married when they're ready to have kids, which I'm not ruling out."

However, in a more recent interview with Howard Stern last fall, Hamm signaled that he had turned a major corner in his life: 

"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," Hamm told Stern, adding that he's "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?"

We wish Jon Hamm and Anna Osceola the best with their engagement. 

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