Jon Hamm and Anna Osceola may soon be taking on an exciting new role together: parenthood.
Multiple outlets reported on Monday, August 10, that Osceola, 38, is pregnant with the couple’s first child.
The pregnancy reports surfaced after Osceola was photographed during a recent Hamptons getaway with Hamm, 55. Photos published by the Daily Mail appeared to show Osceola with a growing baby bump as she and her husband spent time together by the ocean.
Us Weekly reported that it had reached out to Hamm’s representative for comment.
If confirmed, the pregnancy would mark a meaningful new chapter for the couple, particularly after Hamm has spoken openly in recent years about marriage, family and his hopes of eventually becoming a father.
Hamm and Osceola first crossed paths while working on the 2015 series finale of Mad Men. Osceola appeared as a receptionist named Clementine, while Hamm famously starred as advertising executive Don Draper throughout the acclaimed AMC drama’s run from 2007 to 2015.
The two were romantically linked in 2017, and their relationship later became public.
As their romance grew more serious, Hamm began discussing how his outlook on relationships and family had changed over time.
During a 2022 interview with Howard Stern, Hamm explained that working through difficult experiences from his past had helped him become more open to building a future with Osceola.
He said the relationship had opened up the possibility of “being married, having kids” and creating what he described as a new version of happiness, life and wellness.
That possibility soon became reality in another major way.
Hamm proposed to Osceola, and the couple married in the summer of 2023 in Big Sur, California. Their wedding location also carried special meaning because it was connected to where the Mad Men finale had been filmed.
Following their wedding, reports suggested that starting a family was already on the couple’s minds.
A source told Us Weekly in June 2023 that Hamm and Osceola were thinking about having children, adding that the actor felt his marriage represented a fresh beginning in his life.
Hamm himself became even more direct about fatherhood the following year.
Speaking in June 2024, the actor said he hoped married life with Osceola would eventually “turn into kids.”
He also acknowledged that becoming a father later in life would come with a different experience.
“It’s not lost on me that I’m 53,” Hamm said at the time. “I will be the old dad, but so it goes. It could be a good thing. We’ll see.”
Hamm has also been candid about how seriously he approached marriage.
He previously admitted that proposing to Osceola was frightening for him, in part because his own parents’ marriage had ended after a relatively short period. Even with those fears, Hamm said he eventually realized that wanting to build a life with Osceola was more important than his uncertainty.
Their wedding ultimately became an emotional milestone for the actor.
Hamm recalled being surrounded by the people he loved and said the experience simply “felt right.”
He later described the marriage as a kind of “reset” and “reboot” in his life — a chance to approach his future from a new perspective.
Now, with reports that Osceola is pregnant with their first child, that new chapter may be expanding once again.
For Hamm, who has openly discussed his hopes of becoming a father, the reported pregnancy could represent the family life he once said he was finally ready to imagine.
