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Jon Hamm Is Engaged to ‘Mad Men’ Co-Star Anna Osceola: Report

Osceola appeared in Mad Men’s final episode, where she played a minor role.

Jon Hamm is engaged to his girlfriend of two years, Anna Osceola, People confirmed Monday. The pair reportedly met while on the set of the hit AMC series Mad Men, and started dating in 2020. They also acted together in the 2022 crime comedy Confess, Fletch. Osceola appeared in Mad Men’s final episode, where she played a minor role as a receptionist at a retreat Don Draper, Hamm’s character, attends. He discussed the relationship during an interview last year with Howard Stern, where he suggested that he was coming around to the idea of marriage. “I’m in a relationship right now and it’s comfortable,” he said. “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.” Hamm’s rep, however, has not commented.