Jon Hamm Reflects on Nuptials with Anna Osceola: A Serendipitous Journey Complete

Jon Hamm recently spoke about his "perfect" wedding with actress Anna Osceola, five months after they tied the knot. "It only took me half a century, but I figured I might as well get it right," Hamm, 52, said on the Tuesday, November 28, episode of Jimmy Kimmel Live!

Hamm provided a rare insight into his personal life, sharing details of his meaningful nuptials for the first time. The star-studded June wedding included guests such as John Slattery, Billy Crudup, Paul Rudd, Tina Fey, Brooke Shields, and Larry David. Despite the high-profile attendees, Hamm and his 35-year-old bride, Osceola, intentionally kept the ceremony intimate. "It was a small and great day," he explained.

"Tall Jon," a mutual friend of Hamm and Kimmel, officiated the ceremony, using his height to stand closer to the cliff. Hamm was previously in an 18-year relationship with Jennifer Westfeldt before they split in 2015. He met Osceola while filming the final episode of Mad Men, where she played a receptionist at a retreat attended by Hamm's character, Don Draper. Their romance was confirmed by Us in June 2020, and three years later, Hamm proposed.

Jon Hamm and Anna Osceola. Lionel Hahn/Getty Images

The couple paid homage to their Mad Men origins by holding their wedding at Anderson Canyon in Big Sur, California, the very location where they first met. "It was a complete circle moment," Hamm revealed on Tuesday. "It all came full circle."

When Kimmel playfully inquired about the possibility of receiving a discounted rate due to their association with the venue, Hamm humorously responded, "Absolutely, it was fantastic."

An insider exclusively revealed to Us that the reception following the wedding was a lively affair, with a buzzing dance floor. Another source shared that Hamm and Osceola are already considering starting a family, with the insider noting, "Jon feels like this is the start of something new. He's in a great place, and his friends are thrilled to see him so happy."

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Prior to getting married, the couple kept their relationship fairly private. In September 2022, Hamm admitted during an appearance on The Howard Stern Show that undergoing therapy helped him to become more emotionally open and vulnerable in his relationship with Osceola.