Not only did Jon Hamm win an Emmy for his role as Don Draper on Mad Men, but the show introduced him to his wife, Anna Osceola.
The actors met while filming the series finale of the AMC drama in 2015, as Osceola played Clementine, a receptionist at the retreat Hamm’s character attended.
Though briefly linked in 2017, Us confirmed the couple’s romance in June 2020. Hamm popped the question nearly three years later, and he and Osceola said “I do” in June 2023.
In 2026, multiple outlets reported that Osceola is pregnant with her and Hamm’s first baby. The actress seemingly confirmed the baby news by showing off her growing belly on a trip to the Hamptons with Hamm in August of that same year.
Scroll below to relive Hamm and Osceola’s sweetest relationship moments:
