Jon Hamm and Wife Anna Osceola Expecting Their First Child Together

Jon Hamm is preparing for a brand-new role: father.

The Mad Men star, 55, and his wife, actress Anna Osceola, 38, are expecting their first child together, according to a source who confirmed the news to PEOPLE. The couple has not publicly announced a due date, and representatives for both actors had not commented on the pregnancy at the time of the report.

Baby on the Way

The pregnancy news emerged after Osceola was photographed appearing to show a baby bump during a beach outing in the Hamptons.

The upcoming arrival will be the first child for both Hamm and Osceola.

For Hamm, the news marks a major new chapter after years of speaking openly about his changing views on marriage and parenthood.

From Mad Men to Real Life

Hamm and Osceola’s relationship has a Hollywood connection that goes all the way back to Mad Men.

The two first met in 2015 when Osceola appeared in the series finale as a receptionist at a California retreat visited by Hamm’s character, Don Draper.

They did not begin dating until several years later, reportedly becoming a couple in 2020. They made their relationship public in 2022 before becoming engaged in February 2023.

A Big Sur Wedding

The couple married in June 2023 at Anderson Canyon in Big Sur, California—the same location where their Mad Men story had first brought them together.

Their wedding was attended by several Hollywood friends, including Paul Rudd and Tina Fey.

Hamm previously acknowledged that marriage and fatherhood were ideas he had once viewed differently, but his relationship with Osceola helped change his perspective.

They Already Work Together

The couple has also continued to collaborate professionally.

Osceola appeared alongside Hamm in the 2022 film Confess, Fletch, and the pair currently work together on Apple’s Your Friends & Neighbors, in which Hamm plays a hedge-fund manager whose life takes a dramatic turn.

Osceola has also appeared in television shows including NCIS, Law & Order: Special Victims Unit, Rizzoli & Isles and Bull.

Hamm’s Long-Awaited Step Into Fatherhood

Hamm has previously spoken about the possibility of becoming a father later in life.

In earlier interviews, the actor acknowledged that his age would make parenthood different from the experience he might have had when he was younger, but he also expressed excitement about the possibility.

Now, at 55, Hamm is officially entering that next chapter.

A New Chapter for the Couple

After meeting more than a decade ago, reconnecting years later and marrying in 2023, Hamm and Osceola are now preparing to become parents.

While the couple has kept details of the pregnancy private—including the baby’s due date—the news represents another major milestone in their relationship.

For the actor best known for playing the complicated Don Draper, fatherhood will bring a role that is far removed from anything he has played on screen: becoming a dad for the first time.