Jon Hamm Opens Up About the 'Thrilling' Newlywed Journey with Wife Anna Osceola, Overlooking Their 6-Month Milestone

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Jon Hamm is loving his new role of husband to wife Anna Osceola.

Hamm and Osceola, 35, crossed paths in 2015 during the filming of the final season of Mad Men. They were briefly connected in 2017, and their relationship was confirmed by We in June 2020. After almost three years of dating, Hamm proposed to Osceola, and the couple got married in June 2023.

Although their semi-anniversary came and went, Hamm admitted to ET that both he and his partner overlooked the relationship milestone. The actor attributed the oversight to the busy holiday season, joking that he even forgot about several recent projects, such as season 5 of Fargo, season 3 of The Morning Show, and the Mean Girls musical movie, set to be released later this month.

Hamm and Osceola initially kept their wedding details private, but Hamm finally opened up about their romance during a November 2023 episode of Jimmy Kimmel Live! "It took me fifty years, but I finally got it right," he said of proposing to his now-wife. He also revealed that their wedding was held at Anderson Canyon in Big Sur, California, the same place where they first met.

“[It was] a full circle moment,” Hamm shared. “It came all the way around.”

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The guest list boasted A-listers such as John Slattery, Billy Crudup, Paul Rudd, Tina Fey, Brooke Shields, and Larry David. Despite the star-studded attendees, Hamm shared that he and his bride chose to keep the ceremony intimate. "We decided to keep it small," he said. "And it was amazing... It was the perfect day."

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After their emotional wedding, a source exclusively told Us that the couple’s reception was lively and the dance floor was always busy. Another insider mentioned that Hamm and Osceola are considering starting a family, saying, “Jon feels like this is just the beginning. He’s happy and in good health, and his friends are thrilled to see him this way.”

Before his relationship with Osceola, Hamm had been with Jennifer Westfeldt for 18 years. In 2015, the couple announced their separation with a statement saying, “With deep sadness, we have chosen to part ways after 18 years of love and shared history. We will continue to support each other in every way possible going forward.”