Jon Hamm, 55, and wife Anna Osceola, 38, expecting their first child together

Jon Hamm and Anna Osceola wed at Anderson Canyon in Big Sur, the same location where the 'Mad Men' finale was filmed, surrounded by celebrity friends
Jon Hamm and Anna Osceola got married in June 2023 (Getty Images)
Jon Hamm and Anna Osceola got married in June 2023 (Getty Images)

LOS ANGELES, CALIFORNIA: Jon Hamm, 55, is reportedly expecting his first child with his 38-year-old wife Anna Osceola. 

The good news in the life of the couple came three years after they got married in June 2023, the Daily Mail reported.

John Hamm reveals he's ready to be an old dad

Their wedding happened at Anderson Canyon in Big Sur as names like Billy Crudup, Paul Rudd, and Tina Fey witnessed them exchanging vows. Soon after the big day, Hamm sat down with The Hollywood Reporter and shared how he used to think of marriage.

SAN DIEGO, CALIFORNIA - MAY 04: (L-R) Jon Hamm and Anna Osceola attend the Global Premiere of
Jon Hamm and Anna Osceola attend the 'Top Gun: Maverick' world premiere on May 04, 2022 in San Diego, California (Getty Images)

“I didn’t look at marriage as a thing. Obviously, my parents were not married long, so I don’t have a model to look at and go, ‘Oh, this is how one finds happiness.’ 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 revealed.

The ‘Mad Men’ star further hoped that his union with Osceola “turns into kids. 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.”

John Hamm was not sure about having children earlier

But years ago, Hamm was not pro-kids. In 2008, he told The Guardian, “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. I think when people come from a stable family having children becomes a celebration and I'm not sure it would be that way for me,” he had added.

Jon Hamm and Jennifer Westfeldt attend the
Jon Hamm and Jennifer Westfeldt attend the 'Girls' season four series premiere after party at The Museum of Natural History on January 5, 2015 in New York City (Photo by Jamie McCarthy/Getty Images)

Before meeting his current wife, the ‘Your Friends and Neighbors’ actor was in a long-term relationship with Jennifer Westfeldt. 

They were together from 1997 to 2015. During that time, Hamm had reportedly said in an interview that he did not “have the marriage chip, and neither of us have the greatest examples of marriages in our families.”

John Hamm felt 'very settled and comfortable' after meeting Anna Osceola

But years later in 2022, Hamm changed his stance during an interview with Howard Stern on his SiriusXM show.

Jon Hamm attends Apple TV+'s
Jon Hamm attends Apple TV+'s 'Your Friends & Neighbors' New York Premiere at DGA Theater on April 08, 2025 in New York City (Photo by Theo Wargo/Getty Images)

“This is another place in my life that I feel very settled and comfortable. I’m in a relationship right now and it’s comfortable. I'm now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness,” he stated at the time.

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