Jon Hamm and Anna Osceola are engaged after two years of dating, per . The couple first met on the set of in 2015. Hamm's rep has not responded to a request for comment.
Osceola, 34, appeared as a guest in 's final episode. She played a receptionist at the retreat center that Hamm's character, Don Draper, attended.
Several months later, Hamm, 51, separated from his girlfriend of 18 years, Jennifer Westfeldt. He and Osceola were not romantically linked until five years later, in 2020.
In September 2022, the couple appeared together onscreen again in the comedy crime film Several months prior, they walked their first-ever red carpet together at an Oscars after-party in March.
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