Jon Hamm, 55, Expecting First Child: Wife Anna Osceola Shows Baby Bump
Jon Hamm Is Going to Be a First-Time Dad at 55!
The Big News
Jon Hamm—the actor famous for playing Don Draper on Mad Men—is about to start his most important role yet: dad.
According to The Daily Mail, Hamm’s wife, Anna Osceola, is pregnant with their first baby. Photographers spotted her growing baby bump during a beach day in the Hamptons last week. This wasn’t the first clue—the couple was also photographed in Ischia, Italy, back in late June, where Osceola already appeared to be expecting.
Important Point
Jon Hamm is 55 years old. This will be his very first child. Anna Osceola is 38.
A Long Road to "Yes"
Hamm hasn’t always been sure about fatherhood. In fact, back in 2008, he told The Guardian:
"I don’t necessarily want kids. A lot of our friends are having children and I don’t know if it’s for me. I haven’t come down hardcore on either side of the argument."
At the time, he was in a long-term relationship with Jennifer Westfeldt. They were together for nearly 20 years before splitting up in 2015.
How He Met Anna
Here’s the sweet part: Hamm met Osceola on the set of Mad Men in 2015—the very same year the show ended and his long-term relationship ended.
- Osceola had a tiny role in the series finale (she played a receptionist in one episode).
- They didn’t start dating until 2020.
- They got married in June 2023 in Big Sur, California—at the exact location where the Mad Men finale was filmed.
Hamm later called the wedding "a reset, a reboot, a reframe, a reimagining"—almost exactly nine years after the show wrapped.
He Changed His Mind
In a 2024 interview with The Hollywood Reporter, Hamm (then 53) opened up about how much his thinking had shifted:
"And my wedding day was perfect. Everybody I love was there. It was so emotional, and it felt right. I was like, ‘OK, I guess this is a thing.’"
He also admitted fatherhood was on his mind—even with the reality of his age:
"So, it’s been great. And I hope it turns into kids. It’s not lost on me that I’m 53."
Well, hope turned into reality.
They Work Together, Too
The couple now share the screen on Apple TV+’s Emmy-winning series Your Friends & Neighbors. So they’re not just building a family—they’re building a creative partnership, too.
Quick Timeline: Jon & Anna’s Journey
| Year | Milestone |
|---|---|
| 2015 | Meet on Mad Men set (final season) |
| 2015 | Hamm splits from Jennifer Westfeldt (18-year relationship) |
| 2020 | Begin dating |
| June 2023 | Marry in Big Sur, CA (Mad Men finale location) |
| 2024 | Hamm says he hopes for kids "soon" |
| June 2024 | Spotted in Italy—Osceola appears pregnant |
| August 2024 | Baby bump visible in Hamptons; pregnancy confirmed |
Summary
- Jon Hamm (55) and Anna Osceola (38) are expecting their first baby together.
- The news was confirmed after photos showed Osceola’s baby bump in the Hamptons (August 2024).
- Hamm was once unsure about having kids—but marriage and time changed his perspective.
- They met on the Mad Men set in 2015, started dating in 2020, and married in 2023.
- The wedding took place at the Mad Men finale location—a full-circle moment.
- They now co-star on Your Friends & Neighbors.
FAQ
How old is Jon Hamm?
He’s 55. This will be his first child.
Who is Anna Osceola?
She’s an actress (38) who had a small role in the Mad Men series finale. She and Hamm met on set in 2015.
Were they together for a long time before getting married?
They started dating in 2020 and got married in June 2023—so about three years.
Did Jon Hamm have kids with his ex-partner Jennifer Westfeldt?
No. They were together for nearly 20 years but never had children.
Where did they get married?
Big Sur, California—at the same location where the Mad Men finale was filmed. Hamm called it a "reboot" nine years later.
Source: InTouch Weekly