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Reading: Why Jon Hamm Changed His Mind About Having Kids Since He Met Wife Anna Osceola (Exclusive)
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The Hollywood Ear > News > Why Jon Hamm Changed His Mind About Having Kids Since He Met Wife Anna Osceola (Exclusive)
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Why Jon Hamm Changed His Mind About Having Kids Since He Met Wife Anna Osceola (Exclusive)

News Room By News Room August 13, 2026
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Jon Hamm is “genuinely excited” to become a father now that wife Anna Osceola is pregnant — but he didn’t always plan on having children.

“Jon was in a very different mindset and a different place in his life when it came to having kids in the past,” a source exclusively tells Us.

The insider notes that “years ago” Hamm, 55, “felt differently about whether fatherhood was something he wanted for himself.”

The Mad Men alum’s “perspective has changed a lot since then,” the source adds, revealing that Hamm is in a “completely different place in life now.”

Related: Jon Hamm’s Wife Anna Osceola Is Pregnant, Expecting 1st Baby: Report

Jon Hamm and wife Anna Osceola are preparing for their biggest role yet: parenthood! Multiple outlets reported on Monday, August 10, that Osceola, 38, is pregnant with her and Hamm’s first baby. In photos obtained by the Daily Mail, Osceola showed off a growing baby bump while wearing a bikini during a recent getaway with […]

Hamm’s openness to parenthood has seemingly shifted since Osceola, 38, entered his life.

“Anna has always known that she wanted to have a family, but she was incredibly understanding of where Jon was when they first started dating,” the source tells Us.

The insider explains that becoming a parent was “never something” Osceola “pressured” Hamm about when they were first romantically linked in 2017 after meeting during the final season of Mad Men in 2015. Osceola played Clementine, a receptionist who worked at the spiritual retreat that his character, Don Draper, visited. (Us confirmed in June 2020 that Hamm and Osceola were officially dating.)

“They were very open with each other from the beginning about what they both wanted and how they were feeling,” the source shares, calling the topic “an ongoing conversation.”

As their relationship evolved and their bond strengthened, the insider says that Hamm and Osceola “got to a place together where they both felt ready to take that next step.”

“They’re both so excited and it really feels like the right time for them,” the source tells Us, adding that Hamm “is in a place in his life where he’s ready and genuinely excited to become a dad.”

Us has reached out to Hamm and Osceola’s reps for comment.

Prior to meeting Osceola, Hamm dated Jennifer Westfeldt for 18 years from 1997 to 2015.

Related: Inside Jon Hamm and Wife Anna Osceola’s Decision to Start a Family

Jon Hamm and wife Anna Osceola are excited to expand their family with their first baby after three years of marriage. “Jon has always wanted to be a dad with Anna,” a source exclusively tells Us. “Having a family was something that was really important to both of them from the beginning. They’ve talked about […]

Hamm exclusively told Us his thoughts about parenthood in March 2012, sharing at the time, “I see my friends who have children and I’m like, ‘Dude, how are you even upright, much less here at work at 6 a.m.?’”

Following his split from Westfeldt, 56, in September 2015, Hamm moved on with Osceola, whom he wed in June 2023.

One year after Hamm and Osceola got married, the actor hinted that he had a change of heart when it came to having kids. Hamm told The Hollywood Reporter in June 2024 that he was open to being a first-time dad and embarking on that journey with Osceola.

“I hope it turns into kids,” Hamm said 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.”

News broke on Monday, August 10, that Hamm and Osceola are expecting their first baby together after the actress was photographed wearing a bikini that showed off her growing baby bump.

“Jon has always wanted to be a dad with Anna,” a source exclusively told Us on Monday, noting that Hamm is “over the moon” about becoming a father.

The insider added that Osceola is “pretty far along now and feeling really good” while getting into nesting mode. “They have been trying to relax a bit but are enjoying making plans for the baby.”

Read the full article here

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Related: Jon Hamm’s Wife Anna Osceola Is Pregnant, Expecting 1st Baby: ReportRelated: Inside Jon Hamm and Wife Anna Osceola’s Decision to Start a Family
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