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Jon Hamm, 55, and Wife Anna Osceola, 38, Expecting Baby No. 1 Following Actor's Concerns About Being an 'Old Dad'

Photo of Jon Hamm and Anna Osceola
Source: MEGA

Jon Hamm and his wife, Anna Osceola, are expecting their first child together.

Aug. 10 2026, Published 2:10 p.m. ET

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Jon Hamm is going to be a dad!

The Mad Men actor, 55, and his wife, Anna Osceola, are expecting their first child together nearly three years after tying the knot, sources confirmed to Daily Mail on Monday, August 10.

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Anna Osceola Showed Off Her Growing Baby Bump

Photo of Jon Hamm and Anna Osceola tied the knot in June 2023.
Source: MEGA

Jon Hamm and Anna Osceola tied the knot in June 2023.

New photos showed the 38-year-old actress flaunting her growing baby bump in a green string bikini while enjoying a sunny beach day in the Hamptons.

Meanwhile, her husband complemented her look in a pair of tan swim shorts.

The actress is believed to be in her second trimester.

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Jon Hamm and Anna Osceola Tied the Knot in 2023

Photo of Jon Hamm and Anna Osceola worked together on the series finale of 'Mad Men' in 2015.
Source: MEGA

Jon Hamm and Anna Osceola worked together on the series finale of 'Mad Men' in 2015.

The exciting announcement comes three years after Hamm and Osceola tied the knot in June 2023.

Hamm and Osceola reportedly met while filming the series finale of Mad Men in 2015, where Osceola played a receptionist at an event Hamm's character attended. Their romance wasn't confirmed until 2020 after they were spotted together on multiple occasions.

The pair is known to keep their relationship out of the spotlight, as neither is on social media.

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Jon Hamm Previously Voiced Concerns About Being an 'Old Dad'

Photo of Jon Hamm hoped being an 'old dad' could be a 'good thing.'
Source: MEGA

Jon Hamm hoped being an 'old dad' could be a 'good thing.'

Hamm vulnerably opened up about his concerns about starting a family later in life nearly one year after getting married.

"It’s not lost on me that I’m 53," he said in a June 2024 interview with The Hollywood Reporter. "I will be the old dad, but so it goes. It could be a good thing. We’ll see."

He admitted that his parents' divorce played a role in his formerly pessimistic outlook on kids, but since marrying Osceola, he "hoped [their marriage] turns into kids."

Jon Hamm Didn't 'Necessarily Want Kids'

Photo of Jon Hamm and Jennifer Westfeldt dated from 1997 to 2015.
Source: MEGA

Jon Hamm and Jennifer Westfeldt dated from 1997 to 2015.

Years earlier, the Baby Driver actor shared a much different stance on fatherhood, revealing in a 2008 interview that he wasn't sure he wanted children.

"I don't necessarily want kids. A lot of our friends are having children and I don't know if it's for me," he told The Guardian at the time. "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."

At the time, Hamm was in a long-term relationship with actress Jennifer Westfeldt, whom he dated from 1997 to 2015.

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