Jon Hamm, 55, and Wife Anna Osceola, 38, Are Expecting Their First Child Together
Jon Hamm, 55, and Wife Anna Osceola, 38, Are Expecting Their First Child Together
Hannah MalachMon, August 10, 2026 at 5:42 PM UTC
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Jon Hamm and Anna Osceola on April 14, 2026.Credit: Getty ImagesThe Gist -
Jon Hamm, 55, and Anna Osceola, 38, are expecting their first child, making them both first-time parents.
The couple married in 2023 after meeting on the set of Mad Men.
Osceola, 38, recently debuted her baby bump in the Hamptons.
At 55, Jon Hamm is finally preparing for fatherhood as his wife, Anna Osceola, 38, is pregnant with their first child. The two actors met on the set of Mad Men before tying the knot in 2023.
The news of Osceola’s pregnancy was confirmed by People on August 10. The Your Friends and Neighbors star recently debuted her baby bump at the beach, per the Daily Mail, after being spotted in the Hamptons with Hamm. Osceola rocked a black bikini as she and her husband strolled across the sand. Reps for Hamm and Osceola did not immediately respond to InStyle’s request for comment.
Jon Hamm and Anna Osceola on February 23, 2026.Credit: Getty Images
Osceola appeared on the series finale of Mad Men back in 2015, but it would be years before she and Hamm connected romantically. They were first spotted together in 2017, though their relationship wasn’t publicly confirmed until 2020. The couple made their red carpet debut in 2022, attending an after-party for the Oscars.
Hamm and Osceola became engaged in 2023, wth Osceola debuting her emerald-cut solitaire diamond engagement ring at the annual Vanity Fair Oscar party.
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Anna Osceola and Jon Hamm at the 2026 Vanity Fair Oscar Party on March 15.Credit: Getty Images
Hamm admitted that he was “terrified” to propose in an interview with The Hollywood Reporter in June 2024. “I just remember feeling, ‘This is really scary,’” he said, adding that he grew up with divorced parents. “Then going, ‘Well, it probably means it’s worthwhile.’”
He and Osceola exchanged vows on June 24, 2023, in Big Sur, California, which also happens to be the same location where the Mad Men finale was filmed. Celebrity attendees included Billy Crudup, Paul Rudd, and Tina Fey. Osceola walked down the aisle in a strapless, A-line bridal gown, while Hamm wore a classic black tuxedo. The newlyweds later honeymooned in Mallorca, Spain.
Jon Hamm and Anna Osceola on March 30, 2026.Credit: Getty Images
“Ideally, [marriage] gives you and your partner a sense of stability and comfort and an identifying capacity that is better, deeper, richer than ‘it’s my girlfriend’ or ‘my boyfriend’ or what have you,” Hamm said on the “Table for Two” podcast prior to his wedding.
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