The “Mad Men” star, 55, is expecting his first child with his wife, Anna Osceola, 38. According to The Daily Mail, the couple was recently seen spending time together in the Hamptons, where Osceola’s pregnancy was visible during a beach outing.
Jon Hamm and Anna Osceola’s Relationship Has Come a Long Way
Hamm and Osceola’s relationship dates back nearly a decade, when the two actors first crossed paths while working on “Mad Men” in 2015. Osceola appeared in the series finale as Clementine, a receptionist at the retreat where Hamm’s Don Draper spends time. Their connection initially remained out of the spotlight, and the pair were only briefly linked publicly in the years that followed.
By 2020, Hamm and Osceola were spending more time together, with their relationship becoming increasingly difficult to keep private. They made their red carpet debut as a couple at an Oscars viewing event in 2022, marking a more public stage in their relationship.
The couple took another significant step in February 2023, when Hamm proposed to Osceola. Several months later, they married in June 2023 in Big Sur, California. The location carried a connection to their shared history, as the “Mad Men” finale had also been filmed there.
Now, three years after their wedding, Hamm and Osceola are preparing to welcome their first child together. The pregnancy was reported after the couple’s Hamptons outing, with photographs showing Osceola with a visible baby bump. Neither has publicly announced additional details about the pregnancy at this time.
The news comes as Hamm continues an active period in his career. His recent television work includes “Your Friends & Neighbors,” in which he stars as Andrew “Coop” Cooper, a wealthy financier whose life changes dramatically after losing his job. The show premiered in 2025 and returned for a second season this year, with a third season also in development.
Hamm is also preparing for the premiere of “American Hostage,” an upcoming crime thriller anthology series in which he plays Indianapolis radio reporter Fred Heckman. The title is scheduled to debut on MGM+ on September 20.