Jon Hamm and Wife Anna Osceola Expecting Their First Child Three Years After Big Sur Wedding

Jon Hamm and Anna Osceola are preparing to become parents for the first time.

The Mad Men star and his wife are expecting their first child together, a source confirmed to PEOPLE, marking a major new chapter for the couple three years after they married in California.

Hamm, 55, and Osceola, 38, have not publicly commented on the pregnancy. Representatives for both actors could not be reached for comment.

The Daily Mail was first to report that the couple are expecting a baby.

The news comes after years in which Hamm has spoken openly about how his views on marriage, family and fatherhood changed as his relationship with Osceola became more serious.

A New Chapter After Their 2023 Wedding

Hamm and Osceola married in June 2023, several months after news of their engagement emerged that February.

Their wedding took place at Anderson Canyon in Big Sur, California, a location with special significance to Hamm’s career.

The picturesque site was also used during the filming of the finale of Mad Men, the acclaimed AMC series that made Hamm internationally famous through his role as advertising executive Don Draper.

The ceremony reportedly included several famous friends, with Billy Crudup, Paul Rudd and Tina Fey among the guests.

According to TMZ, Hamm and Osceola also incorporated another cinematic reference into the celebration.

Their walk-up song was reportedly the theme from the 1967 James Bond film “You Only Live Twice.”

The wedding represented a significant personal milestone for Hamm, who had previously spoken about his complicated feelings toward marriage.

Not long afterward, he began discussing the possibility that marriage could eventually lead to children.

Hamm Had Already Spoken About Becoming a Father

In an interview with The Hollywood Reporter around the time of his wedding, Hamm reflected on how his childhood had influenced his earlier views about marriage.

The actor explained that because his parents divorced when he was young, he had not always viewed marriage as something he necessarily wanted for himself.

His perspective changed over time.

After marrying Osceola, Hamm said he hoped their relationship might eventually grow into something even bigger.

He specifically mentioned the possibility of having children.

“It’s not lost on me that I’m 53,” Hamm said at the time.

He acknowledged that if he became a parent, he would be an older father.

“I will be the old dad, but so it goes,” he said. “It could be a good thing. We’ll see.”

Now, several years after those comments, the possibility Hamm once discussed has reportedly become reality.

How His Relationship With Osceola Changed His Outlook

Hamm had previously offered a deeper look at his relationship with Osceola during a September 2022 appearance on Howard Stern’s SiriusXM show.

At that point, the couple were not yet married, but Hamm made it clear that the relationship had fundamentally changed how he thought about his future.

He described feeling settled and comfortable in his personal life and said that emotional stability had allowed him to seriously consider milestones that once seemed less certain.

“This is another place in my life that I feel very settled and comfortable,” Hamm said. “I’m in a relationship right now and it’s comfortable.”

He explained that personal reflection had made the relationship more meaningful and opened him to possibilities including marriage and children.

For Hamm, those ideas were connected to a broader effort to redefine what happiness and emotional well-being looked like in his life.

He spoke about “defining a new version of happiness, life, wellness” and said that building that kind of future had become something he was actively working toward.

When Stern asked whether he was in love with Osceola, Hamm answered emphatically that he was “very much so.”

Those remarks became especially significant when the couple announced their engagement several months later.

From ‘Mad Men’ Connection to Real-Life Marriage

Hamm and Osceola also share a professional connection.

Osceola appeared in the 2015 series finale of “Mad Men,” although the couple’s relationship developed later.

Their eventual wedding at Anderson Canyon provided a subtle full-circle connection to the series.

Hamm had spent years portraying Don Draper, one of television’s most complicated fictional husbands and fathers, while his own views about marriage remained far more cautious.

Years later, he returned to a location associated with the end of that character’s story to begin a very different chapter in his own life.

Marriage was not the end of their professional overlap, either.

The couple have since worked together again on “Your Friends & Neighbors.”

Working Together on ‘Your Friends & Neighbors’

Hamm stars in the series as Andrew “Coop” Cooper, a former hedge fund manager who turns to theft after his personal and professional life begins to unravel.

Osceola plays Maggie Haber, a member of Coop’s wealthy neighborhood social circle.

This past April, Hamm spoke to PEOPLE about what it was like having his wife join him while filming the show’s second season.

“It was great to have my wife, Anna, come in and be a part of it,” he said.

For Hamm, working together came with both personal and practical advantages.

“It’s fun to go to work together,” he explained.

The couple were even able to bring their dog to the set on occasion.

“We get to bring the dog in as well sometimes, so that’s nice,” Hamm joked. “We save money on dog sitting.”

There was another benefit to sharing the same workplace.

Hamm said that because Osceola already knew exactly what had happened during his workday, the couple did not need to spend time catching each other up afterward.

He joked that they could avoid having “an hour long conversation on what I did at work.”

“We can save all that time,” he said. “It’s great.”

A Major Personal Milestone for Hamm

The pregnancy news marks an especially notable development because Hamm spent much of his earlier adult life expressing uncertainty about conventional family milestones.

His public comments over the past several years have charted a gradual change.

By 2022, he was openly talking about marriage and children.

By February 2023, he and Osceola were engaged.

They married four months later in June 2023.

Soon afterward, Hamm publicly acknowledged that he hoped fatherhood might eventually become part of their life together.

Now, the couple are reportedly preparing to welcome their first child.

Neither Hamm nor Osceola has shared further details publicly about the pregnancy, including the baby’s expected arrival date.

For the actor, however, the news appears to complete a personal evolution he had already begun describing years earlier.

From once questioning whether marriage was something he wanted at all to publicly imagining himself as an “old dad,” Hamm has gradually embraced a version of family life that once seemed uncertain.

Now, he and Osceola are entering that next chapter together.