‘Mad Men’ Actor Jon Hamm’s Wife Anna Osceola Is Pregnant, Expecting 1st Baby: Report

Us confirmed in February 2023 that Hamm proposed to Osceola. The couple tied the knot that summer.

“He and Anna are thinking of having kids soon,” a source exclusively told Us in June 2023 after the nuptials in Big Sur, California. “Jon feels like this is the beginning. He’s happy and healthy, and his friends love seeing him like this.”

One year later, Hamm spoke about his desire to become a father, calling it the next step he hoped to take with Osceola.

“I hope it turns into kids,” he told The Hollywood Reporter in June 2024. “It’s not lost on me that I’m 53. I will be the old dad, but so it goes. It could be a good thing. We’ll see.”

Hamm also gushed about his wedding with Osceola, confirming he was “terrified” to propose since his parents’ marriage ended after only a short period of time.

“I just knew at a certain point I wanted to be with this person. But when I proposed, I was terrified. I was like, ‘What am I doing?’” he recalled.

Despite not having a “model” to look to for the big moment, Hamm said he knew his fear meant it was “worthwhile” and he took the plunge.

“Everybody I love was there. It was so emotional, and it felt right. I was like, ‘OK, I guess this is a thing,’” the Morning Show alum said of his and Osceola’s wedding. “We did it [where they had shot the Mad Men finale], which was also amazing.”

Hamm added, “Again, it was like a reset, a reboot, a reframe, a reimagining, nine years later, almost to the day. So, it’s been great.”