Jon Hamm recently opened up about the anxiety he felt before proposing to his now-wife, Anna Osceola. In an interview with The Hollywood Reporter, the 53-year-old actor shared that his parents’ early divorce left him without a clear model for a happy marriage. This lack of a blueprint made the idea of marriage daunting for him.
Hamm and Osceola, who is 36, first crossed paths when she appeared in the final episode of Hamm’s iconic AMC series, Mad Men, which concluded in 2015. However, their romantic relationship didn’t blossom until 2020. By February 2023, the couple was engaged, and they tied the knot on June 24, 2023, at Anderson Canyon in Big Sur, California—the very location where the Mad Men finale was filmed.
Reflecting on his proposal, Hamm admitted he was terrified. “I just remember feeling, ‘This is really scary,'” he said. Despite his fears, he realized that the fear likely meant the decision was worthwhile. Hamm described his wedding day as perfect, filled with emotion and surrounded by loved ones. The event felt like a significant reset, almost nine years to the day after the Mad Men finale.
Hamm also expressed his hopes for starting a family with Osceola, acknowledging that at 53, he would be an older dad. “It’s not lost on me that I’m 53. I will be the old dad, but so it goes,” he said. He remains optimistic about the future, hoping that their marriage will lead to children.
The actor’s candidness about his fears and hopes offers a glimpse into his personal life, which he has largely kept private. Hamm’s previous long-term relationship with Jennifer Westfeldt ended in 2015 after 18 years. His relationship with Osceola has been more public, with the couple making appearances at events like the 2024 SAG Awards and sharing moments from their honeymoon in Mallorca.
Hamm’s reflections on marriage and family come at a time when he is enjoying both personal and professional success. He recently starred in the latest seasons of Fargo and The Morning Show, and he continues to be a prominent figure in Hollywood.
In a conversation with PEOPLE in December 2023, Hamm shared his joy about spending the holidays with Osceola, emphasizing the simple pleasure of being together. “The best part of it is just being together. That’s really it,” he said. He also expressed excitement about creating new traditions as a married couple.
Hamm’s journey to marriage and his reflections on the experience highlight the complexities and emotions involved in such a significant life decision. Despite his initial fears, Hamm’s marriage to Osceola appears to be a source of great happiness and fulfillment for the actor.
