Jon Hamm and Anna Osceola are expecting their first child together, marking a major personal milestone for the couple three years after their wedding in Big Sur, California. Osceola debuted her baby bump on September 14, 2026, at the Emmy Awards, where she and Hamm walked the red carpet together before celebrating his work on the series Your Friends & Neighbors. The public appearance followed reports in August confirming that the couple was preparing to become parents.
Red Carpet Debut and Emmy Night Reveal
While the couple has confirmed the pregnancy, they have not publicly announced a due date or the sex of the child, maintaining the private approach that has characterized their relationship throughout their engagement and marriage.
Embracing Fatherhood at Fifty-Five
The milestone follows a long-standing shift in how Hamm views family life. At 55, the actor has spoken openly about coming to terms with becoming an older father, noting during a September appearance on NBC’s Today that he has spent much of his life around children through teaching, nieces, and nephews.
"The best thing I keep hearing is how much it changes you for the better, and I’m excited," Hamm told Today host Craig Melvin, describing the upcoming phase as both "thrilling and terrifying."
During an appearance on Late Night with Seth Meyers, he similarly described himself as very excited and deeply terrified. Hamm was born on March 10, 1971, while Osceola is 38. Reflecting on the timing in a 2024 interview with The Hollywood Reporter, Hamm acknowledged that he would be an older parent, but added, "It could be a good thing. We’ll see."
From Mad Men Set to Big Sur Wedding
The couple’s relationship began through the professional world of television. They first crossed paths on the set of Mad Men, the AMC series that made Hamm a global television star. Osceola appeared in the 2015 series finale as Clementine, a receptionist at the California retreat where Don Draper experiences the emotional breakthrough that concludes the show.
At the time, Hamm was in a long-term relationship with actress Jennifer Westfeldt, which ended later that year after nearly two decades together. Hamm and Osceola were subsequently seen together several times before their romance became public in 2020. They made their red-carpet debut in 2022 and co-starred in the crime comedy feature Confess, Fletch.
In February 2023, the couple became engaged. They married later that year in June at Anderson Canyon in Big Sur—the exact location connected to the Mad Men finale where they had first worked together.
Overcoming Past Hesitations
Hamm previously admitted that his perspective on marriage and family changed significantly through his relationship with Osceola. Speaking with Howard Stern in 2022, he shared that being with her had opened up the possibility of marriage and children, concepts he had viewed with caution earlier in his life due to losing both of his parents before reaching adulthood and experiencing his parents’ divorce when he was young.
Collaborating On and Off Screen
Alongside their personal milestones, the couple has continued to share professional projects. In addition to Confess, Fletch, both actors joined the cast of Apple’s Your Friends & Neighbors, where Hamm stars as Andrew “Coop” Cooper and Osceola appears as Maggie Haber.
Hamm has previously noted the practical benefits of working alongside a spouse, explaining that sharing a production schedule helps mitigate the prolonged separations often caused by demanding filming timelines.
