Jon Hamm's Wife Anna Debuts Baby Bump At Emmys 2026, Actor Once Said He'd Be A 'Terrible Father'
Parents-to-be Jon Hamm and his wife, Anna Osceola, are embracing parenthood for the first time, and the couple made their first red carpet appearance after the news last month.
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Add BollywoodShaadis on GoogleJon Hamm and Anna Osceola are beaming with excitement as they count down the days to holding the hand of their first child. The Your Friends & Neighbors stars arrived with a very special plus-one at the 2026 Emmy Awards as they stepped onto the red carpet on Monday night.
Osceola proudly cradled her growing baby bump as she posed alongside Hamm. While this is an exciting moment for the father-to-be, he was once sceptical about being a dad.
Jon Hamm is 'over the moon' for embracing fatherhood with Anna Osceola
On September 14, 2026, the couple made their first major public appearance after the pregnancy news, arriving hand-in-hand at the Peacock Theater in Los Angeles. Hamm, 55, looked dapper in a classic black tuxedo and bow tie, while Osceola, 38, showed off her bump in an elegant black-and-white patterned halter dress.
The couple, who co-star in the Emmy-nominated series Your Friends & Neighbors, appeared happy and relaxed as they posed for photographers. Osceola had previously been photographed with a visible bump during a getaway with Hamm in the Hamptons, but the Emmys marked her first official red-carpet baby-bump debut.
Speaking about the parents-to-be, an insider told Us Weekly that they are thrilled to be starting a family together. The source shared:
"Jon has always wanted to be a dad with Anna. Having a family was something that was really important to both of them from the beginning. They’ve talked about this chapter for a long time and were always on the same page about wanting children, so for it to actually be happening now feels incredibly special."
The insider further added that Anna Osceola is "pretty far along now and feeling really good" while trying to relax and "making plans for the baby." This is a far cry from the old Jon, who once openly questioned whether fatherhood was right for him and feared he would be a "terrible father."
Jon Hamm once said he would be a 'terrible father'
Long before he prepared to become a dad, Hamm had been candid about his uncertainty about children. In a 2012 interview with Us Weekly, when he was 41 and dating actress Jennifer Westfeldt, Hamm bluntly said, "I'd be a terrible father!" At the time, the couple had chosen not to have children. Westfeldt also spoke about their decision, explaining that although she had thought about motherhood, she hadn't reached a point of certainty.
Hamm and Westfeldt eventually ended their 18-year relationship in 2015. But years later, the actor's perspective on marriage and children began to change. That shift came after he started dating Osceola.
Jon and Anna first crossed paths while working on Mad Men, where Osceola appeared in the show's finale. They later reconnected romantically and began dating in 2020. In 2022, Hamm told Howard Stern that his relationship with Osceola had changed the way he viewed his future.
“[I’m] really thinking about all that stuff," he said, referring to marriage and children. He added that their relationship had "opened up the possibility" of getting married and having kids.
Just five months after the interview, Hamm proposed. The couple married in June 2023 at Anderson Canyon in Big Sur, the same location where they had first met while filming Mad Men. And now, the couple is ready to step into their roles as parents.
Hamm had already hinted that fatherhood was becoming part of the future he imagined with Osceola. In 2024, he told The Hollywood Reporter, “I hope it turns into kids," while acknowledging that he would be an older father. He 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."
Anna had always wanted to be a mother, but she never pressured Jon about making it a reality right away. And now that they are expecting, Hamm is the happiest father-to-be. The insider noted:
"They’re both soaking it all in and are just so excited to become parents. Their relationship has only gotten stronger, and they feel really lucky to be going through this together."
Congratulations, Jon and Anna!
Image courtesy: X
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