‘Mad Men’ Actor Jon Hamm’s Wife Anna Osceola Is Pregnant, Expecting 1st Baby: Report

Jon Hamm and wife Anna Osceola are preparing for their biggest role yet: parenthood!

Multiple outlets reported on Monday, August 10, that Osceola, 38, is pregnant with her and Hamm’s first baby.

In photos obtained by the Daily Mail, Osceola showed off a growing baby bump while wearing a bikini during a recent getaway with the Mad Men star, 55, to the Hamptons.

Osceola donned a green two-piece swimsuit and Hamm wore gold trunks as the pair took a dip in the ocean together.

Us has reached out to Hamm’s rep for comment.

Hamm and Osceola met while filming Mad Men’s series finale in 2015 when she played receptionist Clementine. Hamm led the AMC drama as Don Draper from 2007 to 2015.

The pair were romantically linked in 2017 before Us confirmed in June 2020 that Hamm and Osceola were a full-fledged couple.

“It’s only been in the last couple of years of me kind of sitting down and really thinking about all that stuff that’s made the relationship that I’m in now, is even more meaningful,” Hamm told Howard Stern in September 2022 of how dealing with his past trauma had influenced his hopes for the future with Osceola. “And opened up the possibility of being married, having kids, defining a new version of happiness, life, wellness. All that stuff, it sounds hokey and whatever, but it’s real.”

Us confirmed in February 2023 that Hamm proposed to Osceola. The couple tied the knot that summer.

“He and Anna are thinking of having kids soon,” a source exclusively told Us in June 2023 after the nuptials in Big Sur, California. “Jon feels like this is the beginning. He’s happy and healthy, and his friends love seeing him like this.”

One year later, Hamm spoke about his desire to become a father, calling it the next step he hoped to take with Osceola.

“I hope it turns into kids,” he told The Hollywood Reporter in June 2024. “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.”

Hamm also gushed about his wedding with Osceola, confirming he was “terrified” to propose since his parents’ marriage ended after only a short period of time.

“I just knew at a certain point I wanted to be with this person. But when I proposed, I was terrified. I was like, ‘What am I doing?’” he recalled.

Despite not having a “model” to look to for the big moment, Hamm said he knew his fear meant it was “worthwhile” and he took the plunge.

“Everybody I love was there. It was so emotional, and it felt right. I was like, ‘OK, I guess this is a thing,’” the Morning Show alum said of his and Osceola’s wedding. “We did it [where they had shot the Mad Men finale], which was also amazing.”

Hamm added, “Again, it was like a reset, a reboot, a reframe, a reimagining, nine years later, almost to the day. So, it’s been great.”