Jon Hamm's Real-Life Wife Is His Former Mad Men Co-Star

Some of the most famous male actors have been long-time bachelors before marrying in their 50s. "Mad Men" star Jon Hamm was one of them. Growing up with divorced parents was one of Hamm's reasons for never marrying while he was in an 18-year relationship with ex Jennifer Westfeldt. However, the Missouri native married fellow actor Anna Osceola at the age of 52 in 2023.

The two actors met each other on the "Mad Men" set in 2015. Osceola was cast as Clementine, a receptionist at a retreat where Hamm's Don Draper goes in the last season. Since he was still with Westfeldt, Hamm didn't have an instant romantic connection with his co-star. The two sparked romance rumors after a night out in 2017, but sources confirmed they were dating in 2020.

The Midwestern actor seemed to overcome his reservations against marriage while dating his then-girlfriend. On a 2022 episode of "The Howard Stern Show," Stern asked if Hamm sees himself marrying and being with one woman for the rest of his life. The actor said yes without hesitation. "I'm in a relationship right now, and it's comfortable," he explained. "It's also been a process of working on myself, my mental health, all the stuff with my therapist." He credited therapy for making him more emotionally available and making his relationship with Osceola "more meaningful."

Jon Hamm happily broke his no marriage rule in 2023 when he wed Anna Osceola in Big Sur, the very location they met while playing Don Draper and Clementine in "Mad Men."In the first year of marriage, Hamm looked forward to having kids with Osceola. "I hope it turns into kids," he told The Hollywood Reporter in 2024. "It's not lost on me that I'm 53. I will be the old dad, but so it goes. It could be a good thing. We'll see." The press later reported that Hamm is a first-time expectant father at 55 years old in 2026.

Although he's excited to be a father, some netizens criticized Hamm for having children with Osceola because of their sizeable age gap and the speculation about his split from Jennifer Westfeldt. One X user wrote, "Jon Hamm being with a woman for 20 years and being very vocally 'child free', then marrying a younger woman and knocking her up at 55 is very ... Don Draper." However, his commitment to Westfeldt didn't align with Don Draper's womanizing ways. Westfeldt also expressed more uncertainty about having children than Hamm did.

Hamm doesn't seem concerned about the haters while anticipating the birth of his first child. In August 2026, a close source told People about how he's ready to be a dad. "Jon's incredibly excited. This is something he and Anna have wanted and hoped for," the source said. "He's not thinking about his age or what anyone else has to say about it. He's just really happy."