The 'Your Friends and Neighbors' star was previously in an 18-year relationship with his actress Jennifer Westfeldt
The 'Your Friends and Neighbors' star was previously in an 18-year relationship with his actress Jennifer Westfeldt
Published Aug 11, 2026 • Last updated 1 day ago • 2 minute read
US actor Jon Hamm and Anna Osceola attend the Academy Museum Gala at the Academy Museum of Motion Pictures in Los Angeles on October 18, 2025. Photo by Valerie Macon/AFP /Getty ImagesSee more Toronto Sun on Google — save as a Preferred Source
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Jon Hamm and Anna Osceola are having a baby.
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The couple is expecting their first child together, a source told People, though the Daily Mail first reported the news on Monday with photos of Hamm, 55, and Osceola, 38, vacationing in the Hamptons last week.
Hamm, who reportedly first crossed paths with fellow actor Osceola on the set of Mad Men but didn’t begin dating until 2020, were married in June 2023 in Big Sur — the same place where the AMC series finale was filmed. (Osceola played receptionist Clementine in that final episode.)
The Your Friends and Neighbors star was previously in an 18-year relationship with his actress Jennifer Westfeldt. They split in September 2015.
Love and marriage…When discussing his relationship with Osceola in 2022, Hamm said he was “very settled and comfortable” with her.
“[I’m] really thinking about all that stuff,” he said during an appearance on Howard Stern’s SiriusXM show.
“That’s made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.”
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Anna Osceola and Jon Hamm attend SiriusXM Presents SmartLess Live with special guest Howard Stern at The Stephen Talkhouse on August 17, 2024 in Amagansett, New York. (Bryan Bedder/Getty Images for SiriusXM) Photo by Bryan Bedder /Getty Images for SiriusXM… and a baby carriageA year after their wedding, he opened up to The Hollywood Reporter about his desire to have kids with his wife.
“I didn’t look at marriage as a thing,” the Morning Show actor told the outlet, noting his own parents’ divorce didn’t give him a “model to look at and go, ‘Oh, this is how one finds happiness.’
As for Osceola, he just knew he wanted to be with her.
“But when I proposed, I was terrified. I was like, ‘What am I doing?’”
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When asked what he was afraid of, Hamm said he didn’t know.
“I just remember feeling, ‘This is really scary.’ Then going, ‘Well, it probably means it’s worthwhile,’” he recounted.
“And my wedding day was perfect,” Hamm continued. “Everybody I love was there. It was so emotional, and it felt right.”
The Tag actor told THR that he hoped his union with Osceola union “turns into kids.”
Hamm added at the time: “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.”
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