Jon Hamm Breaks Silence on ‘Perfect’ Anna Osceola Wedding
Five months after tying the knot with actress Anna Osceola, Jon Hamm is finally opening up about the couple’s “perfect” wedding.
“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 went on to give a rare glimpse into his personal life, detailing the meaningful nuptials for the first time. The June wedding boasted a star-studded guest list including John Slattery, Billy Crudup, Paul Rudd, Tina Fey, Brooke Shields and Larry David, but Hamm said he and Osceola, 35, purposely kept the ceremony intimate.
“By our decision, it was small,” he explained. “Man, it was great … It was the perfect day.”
Jon Hamm and Anna Osceola's Relationship Timeline
Not only did Jon Hamm win an Emmy for his role as Don Draper on Mad Men, but the show introduced him to his wife, Anna Osceola. The actors met while filming the series finale of the AMC drama in 2015, as Osceola played Clementine, a receptionist at the retreat Hamm’s character attended. Though briefly […]
The ceremony was officiated by “Tall Jon” — a mutual friend of Hamm’s and Kimmel’s — and his height came in handy. “I think he was about 6’10” and we made him stand closer to the cliff,” Hamm joked.
Hamm was previously in an 18-year relationship with Jennifer Westfeldt before the pair called it quits in 2015. He went on to meet Osceola while filming the final episode of Mad Men, in which she played a receptionist at the retreat attended by Hamm’s character, Don Draper. Us confirmed their romance in June 2020, and Hamm popped the question three years later.
Honoring their Mad Men roots, the couple’s wedding took place at Anderson Canyon in Big Sur, California, the same place their meet-cute occurred.
“[It was] a full circle moment,” Hamm shared on Tuesday. “It came all the way around.”
When Kimmel jokingly asked whether the pair got a discount because of their connection to the venue, Hamm replied, “Yes, it was great.”
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He painted a more detailed picture of the ceremony, teasing, “It is still a beautiful property right on the Pacific Ocean, we got married on a cliff and we chose to walk the correct way after we got married.”
Following the wedding, an insider exclusively told Us that the reception “was a blast and the dance floor was energetic at all times.”
According to a second source, Hamm and Osceola are already thinking about having kids. “Jon feels like this is the beginning,” the insider shared. “He’s happy and healthy, and his friends love seeing him like this.”
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Before becoming husband and wife, the twosome kept their relationship relatively under the radar. In September 2022, Hamm confessed on The Howard Stern Show that therapy allowed him to open up emotionally and be more vulnerable in his romance with Osceola.
“It’s only been in the last couple of years of me kind of sitting down and really thinking about all that stuff that’s made the relationship that I’m in now, is even more meaningful, and opened up the possibility of being married, having kids, defining a new version of happiness, life, wellness,” he said.
