Anna Osceola was seen with a visible baby bump during a beach day in the Hamptons last week, and the report on Monday, August 10 said she is expecting her first child with Jon Hamm. For a couple that has kept much of its private life tight, the timing matters because the bump had already been visible in late June.
Hamptons, late June
Osceola is 38 years old, and the pregnancy report turns a set of photographs into a clear family milestone for Hamm. The couple had previously been photographed in Ischia, Italy, in late June, when she first appeared pregnant, before the beach-day images made the story hard to miss.
Jon Hamm in 2008
Hamm’s public view on fatherhood has not always pointed in the same direction. In 2008, while he was still with Jennifer Westfeldt, he said, “I don't necessarily want kids. A lot of our friends are having children and I don't know if it's for me. I haven't come down hardcore on either side of the argument.”
That changed in tone by 2024, when he said, “And my wedding day was perfect. Everybody I love was there. It was so emotional, and it felt right. I was like, 'OK, I guess this is a thing,'” and then added, “So, it's been great. And I hope it turns into kids. It's not lost on me that I'm 53,” in a separate interview.
June 2023 and Your Friends & Neighbors
Hamm and Osceola married in June 2023 in Big Sur, California, after meeting in 2015 on the set of Mad Men and beginning to date in 2020. They now share the screen on Apple TV's Your Friends & Neighbors, which keeps their partnership in view even as the baby report shifts the focus from work to family.
The couple spent nearly two decades in Hamm’s long relationship with Jennifer Westfeldt before splitting in 2015, so this is the first reported child together and a notable change in his personal timeline. The practical question now is simple: when is Anna Osceola due? The report does not give a date, so the next hard fact will come only if they choose to speak further or appear publicly again.
