Everything Jon Hamm has said about becoming a dad as he prepares for fatherhood at 55

Jon Hamm is preparing for a role unlike any he has taken on before: becoming a father for the first time at 55. The Mad Men actor and his wife, Anna Osceola, 38, are expecting their first child together, with the happy news confirmed after Anna was photographed displaying her growing baby bump during a beach outing in the Hamptons.

It marks a particularly poignant new chapter for Jon, whose feelings about marriage, children and creating a family have changed considerably over the years.

Long before meeting Anna, the actor was candid about the fact that he wasn’t convinced fatherhood was for him. After losing his mother when he was just ten and his father when he was 20, Jon admitted his own childhood had shaped the way he viewed family life.

However, in recent years his stance has shifted dramatically, and in 2024 he revealed that he actively hoped marriage to Anna would lead to children. Here is everything Jon has said about fatherhood over the years.

Jon Hamm wasn’t always convinced he wanted children

Back in 2010, when Jon was 39 and in a long-term relationship with actress and screenwriter Jennifer Westfeldt, he spoke candidly about why becoming a parent wasn’t necessarily part of his plans.

“I like kids,” he told Parade. “But I also like the option to close the door. Becoming a parent is a whole other life, and it doesn’t stop.”

Jon’s feelings were closely connected to his own complicated experience of family.

His parents divorced when he was two, and he was raised primarily by his mother, Deborah, until she died from colon cancer when he was ten. Jon then moved in with his father and grandmother, before losing his father while he was at university.

“Losing both parents at a young age gave me a sense that you can’t really control life, so you’d better live it while it’s here,” he explained at the time. “I stopped believing in a storybook existence a long time ago.”

Jon’s views on marriage were equally complicated

For many years, Jon was just as doubtful about marriage. He and Jennifer were together for 18 years, from 1997 until 2015, but never married.

“I don’t have the marriage chip, and neither of us have the greatest examples of marriage in our families,” he told Parade in 2010, adding that Jennifer was nevertheless “the love of my life.”

Jon later explained that his parents’ short-lived marriage had left him without the kind of example he could look towards when imagining his own future. That changed after he fell in love with Anna.

Meeting Anna Osceola changed Jon’s outlook

Jon and Anna first met in 2015 when she appeared in the series finale of Mad Men. They reportedly began dating in 2020 and married three years later at Anderson Canyon in Big Sur, the same location where the show’s famous finale was filmed.

By then, Jon was talking about commitment very differently. Shortly before their wedding, he appeared on the Table for Two with Bruce Bozzi podcast and described marriage as a gateway to a new stage of his life. “[Marriage] is the thing that leads to the next thing of life and that’s what I hope,” he said. “It’s the journey and it’s exciting.”

When Bruce asked whether that next chapter might involve creating a family, Jon’s answer was telling: “TBD… TBD.”

He also described marriage as a “signpost and a signifier of the next chapter”, saying he hoped it would give him and Anna a deeper sense of “stability and comfort”.

Jon admitted he was ‘terrified’ to propose

His transformation from self-confessed marriage sceptic to husband didn’t happen without some soul-searching. In 2024, Jon explained that his childhood continued to influence him even when he knew Anna was the person he wanted to marry.

“Obviously, my parents were not married long, so I don’t have a model to look at and go, ‘Oh, this is how one finds happiness,'” he told the The Hollywood Reporter.

“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?'”

Rather than allowing that fear to stop him, Jon eventually interpreted it differently. “I just remember feeling, ‘This is really scary.’ Then going, ‘Well, it probably means it’s worthwhile.'”

The couple married in June 2023, and Jon later described their wedding as “perfect”, adding: “Everybody I love was there. It was so emotional, and it felt right.”

Jon finally revealed he wanted to become a father

By the following year, Jon’s feelings about children had become far more definitive. Speaking to The Hollywood Reporter, he revealed that he hoped his marriage to Anna would “turn into kids”.

He was also very aware that, should it happen, he would be entering fatherhood considerably later than many men. “It’s not lost on me that I’m 53,” he said at the time. “I will be the old dad, but so it goes.”

Rather than seeing his age entirely as a disadvantage, however, Jon was characteristically open-minded about what it could mean. “It could be a good thing,” he added. “We’ll see.” Two years later, that possibility has become a reality.

At 55, Jon is now preparing to welcome his first child with Anna, more than 15 years after admitting that while he liked children, he wasn’t certain he wanted the all-consuming reality of parenthood.

And perhaps the biggest indication of just how much his outlook has changed came when he reflected on the life he had built with Anna and what he hoped would come next. “This is the exciting part of life,” he said on the Table for Two with Bruce Bozzi podcast. “It’s a signpost and a signifier of the next chapter.”