Jon Hamm and Anna Osceola are expecting their first baby together. The Mad Men star is set to become a first-time father at 55, after Anna, his wife, was recently spotted proudly showing off her growing baby bump at a beach in the Hamptons, the Daily Mail reports. In 2024, Jon opened up about his marriage to Anna, admitting to feeling "terrified" about proposing. Asked whether marriage had been important to him, Jon replied: "I didn’t look at marriage as a thing. "We did it [where they had shot the Mad Men finale], which was also amazing.