The two actors reportedly met in 2015 on the set of Mad Men, when Osceola had a small role as the receptionist at a spiritual retreat Hamm's character, Don Draper, attends in the series finale.

Getty Images The two actors reportedly met in 2015 on the set of Mad Men, when Osceola had a small role as the receptionist at a spiritual retreat Hamm's character, Don Draper, attends in the series ...

By Carly Thomas Associate Editor While Kiernan Shipka appreciates the Mad Men team for trying to shield her from the show’s adult content as a child actor, she admits she kind of understood what ...

Taika Waititi, Rita Ora, Anna Osceola, and Jon Hamm sat together to take in the Game 2 scene. Taika Waititi, Rita Ora, Anna Osceola, and Jon Hamm look on during Game 2 of the 2024 World Series.

Video: Jon Hamm, 53, and wife Anna Osceola, 36, look preppy as they step out together in NYC Jon Hamm and Anna Osceola are arm in arm for their date night at upscale Italian eatery. Jon is dapper ...

Kiernan Shipka, 25, watched Mad Men all the way through for the first time during the COVID-19 pandemic. The Sabrina star started on the wildly popular AMC show when she was six years old and ...