By Page Six | Created at 2026-08-14 03:15:14 | Updated at 2026-08-14 05:17:16
2 hours ago
Jon Hamm was once adamant that he wouldn’t be a good dad.
The actor, 55, is now expecting his first child with his wife, 38-year-old Anna Osceola. But back in March 2012, Hamm declared to Us Weekly in an interview, “I’d be a terrible father!”
At the time, Hamm, who was 41 at the time, was dating actress and filmmaker Jennifer Westfeldt.
That same month, Westfeldt, now 56, opened up about her and Hamm’s decision to not have children in an interview with the New York Times.
“I’ve thought about this a lot lately. I never thought I’d be this age and not have kids,” Westfeldt, who was 42 at the time, admitted. “But my life has also gone in a million ways I never anticipated.”
The “Kissing Jessica Stein” star noted that she didn’t regret the choice.
“I kept feeling like I’d wake up with absolute clarity, and I haven’t,” she explained. “And we have a pretty great life together. The chance that we’ll regret it doesn’t seem like a compelling enough reason to do it.”
Though, she added, “I may wake up tomorrow with that lighting bolt, and I’ll have to scramble to make it happen.”
Hamm and Westfeldt split in September 2015 after 18 years together.
“With great sadness, we have decided to separate, after 18 years of love and shared history,” the pair told Page Six in a joint statement at the time. “We will continue to be supportive of each other in every way possible moving forward.”
Prior to their split, Westfeldt supported the “Mad Men” alum when he went to rehab for a month to treat alcohol addiction in February 2015.
A source recently told Us Weekly that Hamm has definitely changed his mind about being a father.
“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 told the outlet, adding that his “perspective has changed a lot since then” and that he’s in a “completely different place in life now.”
The source also claimed that Osceola never pressured her husband to have kids, though she knew she wanted to have a family.
“[They] got to a place together where they both felt ready to take that next step,” the source said. “They’re both so excited and it really feels like the right time for them.”
“[Hamm] is in a place in his life where he’s ready and genuinely excited to become a dad,” they added.
The couple — who met on the set of “Mad Men” in 2014 — tied the knot in June 2023 after dating for three years.
In September 2022, the actor gushed about Osceola, telling Howard Stern on the latter’s SiriusXM show that she was helping him work on himself.
Osceola “opened up the possibility of things like being married, having kids, you know, defining a new version of happiness, life, wellness,” he shared.
Welcome to the Page Six Community!
Our community is about connecting people through open and thoughtful conversations. We want our readers to share their views and exchange ideas in a safe space.
In order to do so, we've created a simple set of rules that will improve your experience.
Simply put, keep it civil.
Your post will/might be rejected if it contains:
- Spam
- Insults, profanity, incoherent, obscene or inflammatory language and threats of any kind
- Attacks on the identity of other commenters or the article's author
User accounts will/might be blocked if we notice:
- Continuous attempts to re-post comments that have been previously moderated/rejected
- Racist, sexist, or homophobic comments
- Attempts or tactics that put the site security at risk
So, how can you be a power user?
- Stay on topic and share your passion. Feel free to elaborate to get your point across.
- 'Like' or 'Dislike' when you are filled with emotions!
- Protect your community. Use the report tool to alert us when someone breaks the rules.
Thanks for reading our community guidelines. Don't forget, freedom of speech is not the freedom of reach!
