Jon Hamm And Anna Osceola, Once Co-Stars On 'Mad Men,' Are Reportedly Engaged But Not Advertising It

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Brief “Mad Men” co-stars Jon Hamm and Anna Osceola have made a longer-term commitment: They’re reportedly engaged!

People confirmed the news on Monday.

Jon Hamm and Anna Osceola, pictured attending the 2022 ESPYs in Hollywood, are reportedly engaged.
Jon Hamm and Anna Osceola, pictured attending the 2022 ESPYs in Hollywood, are reportedly engaged.

Jon Hamm and Anna Osceola, pictured attending the 2022 ESPYs in Hollywood, are reportedly engaged.

The two worked together on AMC’s Madison Avenue period drama on the last season in 2015. Osceola played a spiritual-retreat receptionist who flirted with Hamm’s Don Draper in the series finale. But romance between the two did not appear to bloom until 2020, Entertainment Weekly noted.

“I’m in a relationship right now ... and it’s comfortable,” Hamm told Howard Stern in 2022. “It’s a feeling of taking care of someone else and being taken care of.”

Osceola also appeared in Hamm’s 2022 comedy “Confess, Fletch.”

The pair went “red carpet official” in 2022, when they appeared hand-in-hand at Vanity Fair’s after-Oscars party.

Hamm, who scored a big hit in 2022 with “Top Gun: Maverick,” previously had a long-term relationship with actor Jennifer Westfeldt that ended in 2015.

Reps for Hamm, 51, and Osceola, 34, haven’t responded to requests for comment from HuffPost and other outlets.

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