Jon Hamm is becoming a first-time father at 55 as his wife Anna Osceola, 38, is expecting their first baby.
Jon Hamm, 53, married actress Anna Osceola, 36, in June 2023. A source confirmed the pregnancy to People on Monday. The couple met while filming the Mad Men series finale in 2015 and confirmed their romance in 2020.
The 53-year-old actor is ready to take the next step in his life and become a father for the first time as he expressed his desire to have children with Anna, 36.
The timing of the announcement comes three years after Hamm dropped hints about their family plans. “[Marriage] is the thing that leads to the next thing of life and that’s what I hope – and it’s the journey and it’s exciting,” he said on iHeartPodcast Table for Two with Bruce Bozzi. “All of the minutiae of planning it and dealing with it can be mind-numbing and all of the other things. But then you understand, and I think it only happened to me, maybe a week [prior] or so, where this sort of calm settled over me.”
Before the wedding, Hamm opened up about his shift in perspective on marriage. Hamm noted that he previously “didn’t look at marriage as a thing.” “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.’ 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.
At the time of the proposal in February 2023, Hamm reflected on his newfound openness to commitment. Since he became a husband, he “hopes [their marriage] turns into kids”. “It’s not lost on me that I’m 53. I will be the old dad, but so it goes,” he told The Hollywood Reporter. “It could be a good thing. We’ll see.”
Before marrying Osceola, Hamm acknowledged that dating fellow actors posed unique challenges. “The funny thing about this career is that there’s no rule book. You really have to lean on one another for their support and for any kind of advice,” he told People.
The Baby Driver star opened up about feeling “terrified” to propose during an interview with The Hollywood Reporter in June 2024. “I just remember feeling, ‘This is really scary,'” he said, adding that he grew up with divorced parents. “Then going, ‘Well, it probably means it’s worthwhile.'”
In the viral moment from three years earlier, during a June 2023 Table for Two podcast interview, Hamm was asked whether he was thinking about having a family. He replied, “TBD.” He described being in an “exciting part of life” characterized by “stability and comfort” and noted that marriage was “the thing that leads to the next thing of life.”
Hamm and Osceola exchanged vows in an outdoor ceremony at Anderson Canyon in Big Sur, California, where the Mad Men finale was filmed. Their celebrity attendees included the likes of Billy Crudup, Paul Rudd, and Tina Fey.
Since the wedding, Hamm has continued to talk about his marriage evolution. Reflecting on his love life, Hamm said “compromise and communication and all the things that you have to relearn, or reteach yourself—it doesn’t come overnight,” He added “It doesn’t come without mistakes and failures, but it’s based on love and a willingness to say, ‘I’ve gotta be able to do better than this, so I need to figure out how I’ve been less-than and work on it.’ And that’s going to therapy and couples therapy, asking, ‘Is it me, is it them, or is it us?’ And it gets better.”
Hamm also reflected on his past relationships when opening up about married life. Hamm was in a long-term relationship with Jennifer Westfeldt before marrying Osceola. The former couple split in 2015 after 18 years together.