Here’s Why People Are Talking About Jon Hamm’s Ex, Jennifer Westfeldt, Amid The News That He’s Becoming A Dad At 55
Дата публикации: 13-08-2026 16:24:47
Jon and his ex, Jennifer Westfeldt, were together for 18 years, but did not marry or have children. He and his wife, Anna Osceola, are currently expecting their first child together.View Entire Post ›
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Here’s Why People Are Talking About Jon Hamm’s Ex, Jennifer Westfeldt, Amid The News That He’s Becoming A Dad At 55Jon and his ex, Jennifer Westfeldt, were together for 18 years, but did not marry or have children. He and his wife, Anna Osceola, are currently expecting their first child together.
Earlier this week, People reported that Jon Hamm and his wife of three years, Anna Osceola, are expecting their first child together.
Jon, 55, and Anna, 38, first crossed paths in 2015 while shooting the last-ever episode of Mad Men, in which Anna had a small role as a receptionist. They were first romantically linked in 2020, and tied the knot three years later — adorably hosting the nuptials at the Mad Men finale filming location in Big Sur, where they first met.
Though the couple is very private, you may have seen that their baby news has sparked a lot of online conversation, with most of the discourse focusing on Jon's age and his past child-free relationship with Jennifer Westfeldt.
For context, Jennifer and Jon were together for 18 years from 1997 to 2015. They were never married and never had children together, which they discussed publicly.
In 2012, Jennifer told the Guardian that she and Jon never got "clarity" about whether they wanted to have kids. "In reality, our lives — Jon's and mine — are so unconventional in every way, it's very difficult," she said. "I think kids should have something grounded. Jon and I are both children of divorce. I'm not sure we can do it without a proper home base."
That same year, Jennifer — who was 42 at the time — said during an interview with the New York Times that she never envisioned herself being child-free in her 40s. "I kept feeling like I'd wake up with absolute clarity [that I want children], and I haven't," she said, explaining that she and Jon had a "pretty great life together," even without kids or marriage. "The chance that we'll regret it doesn't seem like a compelling enough reason to do it. I may wake up tomorrow with that lightning bolt, and I'll have to scramble to make it happen."
So, when Jon and Jennifer announced their split in 2015, there were rumors that the relationship ended because they didn't see eye to eye about starting a family. "There's always been a rift, because he wanted kids and she didn't," a source told Us Weekly amid the breakup.
We obviously can't know this for sure, but what we do know is that Jon was previously wary of marriage (due to the trauma of his parents' divorce when he was young) and once joked that he'd make a "terrible father." "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.?'" he told Us Weekly in 2012, when he and Jennifer were still together.
This all brings us to 2026, where Jon is married and set to become a father at 55 — and people have their thoughts about it. "I knew this day would come," reads one X post with over 10,000 likes. "Deciding to be childfree should always be a deep conviction. So that in twenty years time, when it’s no longer an option for you, and the guy you did no-kids with has a child with a younger woman, your conviction will still be as firm as ever, with no regrets... I’m not criticizing Jon Hamm. I’m happy for him. I’m just recognizing that it might be hard for his Ex. It’s not a good vs evil scenario. Just choices and changes. Life."
To be clear, we don't know whether Jon changed his mind about kids or if he actually wanted them all along — that's between him and Jennifer. But a new report from People suggests that he's "ready" for fatherhood at this stage in his life.
"Jon’s incredibly excited. This is something he and Anna have wanted and hoped for," an insider told the outlet. "He’s not thinking about his age or what anyone else has to say about it... He’s happy, settled, and ready for this. Anna’s amazing, and he feels very lucky that he gets to start a family with her."
After he and Anna tied the knot in 2023, Jon told the Hollywood Reporter that he previously "didn’t look at marriage as a thing." "My parents were not married long, so I don’t have a model to look at," he said. "I just knew at a certain point I wanted to be with this person."
Describing his marriage as a "reset," Jon also expressed his desire to become a father. "It’s been great," he said of married life. "And I hope it turns into kids. 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."
Well, congrats to Jon and Anna!
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