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From Mad Men to marriage: Jon Hamm and Anna Osceola’s love story unveiled

Love is in the air! It seems like Mad Men brought more than just fame and fortune for its star cast. The news that has been doing the rounds in Hollywood for a while now, is that the show’s lead actor Jon Hamm is reportedly engaged to his former co-star Anna Osceola. While the couple hasn’t made an official statement, People Magazine confirmed the news yesterday.

But, that’s not all we’re interested in. Many fans have been curious about Osceola’s role in Mad Men, and we’ve got the answer! The actress played the role of Clementine, a receptionist at a spiritual retreat where Jon Hamm’s character, Don Draper, attended.

Hamm and Osceola first met on the sets of Mad Men in 2015, while he was still in a long-term relationship with Jennifer Westfeldt. After the show wrapped up, they reportedly stayed in touch and were spotted together buying coffee in 2017. It wasn’t until May 2020 when they were spotted hanging out on the beach that rumors about their relationship began to surface.

Since then, the couple has been seen at various events and parties, including the Vanity Fair Oscars party earlier this year. In an interview on Howard Stern’s show, Hamm called their relationship “comfortable” and hinted at the possibility of getting married and having kids.

Before dating Osceola, Hamm was in a long-term relationship with Westfeldt, but they split up amicably. Some reports suggest that their split was due to Jon’s substance issues and frequent partying.

As for Anna Osceola, she is a Massachusetts native who moved to California to pursue an acting career. Her IMDb profile lists her acting credits in shows such as Greek, NCIS, and Law & Order: Special Victims Unit.

We can’t wait to hear more about Hamm and Osceola’s engagement, and we wish them all the happiness in the world!

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