Jon Hamm's Pregnant Wife Anna Osceola Debuts Baby Bump at Emmys 2026

“I didn’t look at marriage as a thing,” Hamm continued. “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.”

As Hamm explained, “When I proposed, I was terrified. I was like, ‘What am I doing?’”

But it was because of that feeling that Hamm knew it was right for him. As he put it, “I just remember feeling, ‘This is really scary,’ Then going, ‘Well, it probably means it’s worthwhile.’” 

For Hamm—who dated Jennifer Westfeldt for nearly 20 years before their 2015 breakup—meeting Osceola marked a shift in his priorities for his personal life. 

"It's only been in the last couple of years, me kind of sitting down and really thinking about all that stuff that's made the relationship that I'm in now even more meaningful," Hamm explained during an appearance on The Howard Stern Show in 2022, “and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness—all that stuff.”

While the Bridesmaids alum admitted that it sounded “hokey” he emphasized that his desire for those things was very “real.”

“It’s what I’m working for,” he continued. “What else is there other than that?”

For more stars on the red carpet, keep reading.