Jon Hamm Explains Why He Was 'Terrified' When He Proposed to Wife Anna Osceola: 'This Is Really Scary'

Hamm and Osceola celebrate their first wedding anniversary on June 24

<p>Christopher Polk/Variety via Getty</p> Jon Hamm (left) and Anna Osceola

Christopher Polk/Variety via Getty

Jon Hamm (left) and Anna Osceola

Jon Hamm is sharing some fears he held about marriage before tying the knot with his wife Anna Osceola.

In a new interview with The Hollywood Reporter, Hamm, 53, opened up about his relationship with Osceola, 36, and the status of his career after starring in the most recent seasons of Fargo and The Morning Show. The actor explained that due to his parents' divorce early in his life, he previously "didn't look at marriage as a thing."

"Obviously, my parents were not married long, so I don’t have a model to look at and go, 'Oh, this is how one finds happiness,' " he said. "I just knew at a certain point I wanted to be with this person. But when I proposed, I was terrified. I was like, 'What am I doing?' "

Hamm and Osceola, who is also an actor, first met when she had a small role in the final episode of Hamm's AMC series Mad Men, which aired its series finale in 2015. The two were not romantically linked until they were seen spending time together in 2020; PEOPLE confirmed they were engaged in February 2023, and Hamm and Osceola held their wedding at Anderson Canyon in Big Sur, California — the site of that Mad Men finale — on June 24, 2023.

Related: Jon Hamm Recalls When a Network Executive Told Him He Would 'Never Be a Television Star': 'He's No Longer at the Head'

<p>Amy Sussman/Getty</p> Jon Hamm and Anna Osceola on March 10, 2024

Amy Sussman/Getty

Jon Hamm and Anna Osceola on March 10, 2024

"I don’t know. I just remember feeling, 'This is really scary,' " Hamm told THR, when asked what he felt "terrified" of when he proposed. "Then going, 'Well, it probably means it’s worthwhile.' And my wedding day was perfect. Everybody I love was there."

"It was so emotional, and it felt right. I was like, 'OK, I guess this is a thing,' " he added. "Again, it was like a reset, a reboot, a reframe, a reimagining, nine years later, almost to the day [of the Mad Men finale.] So, it’s been great."

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Hamm additionally said during the interview that he hopes he and Osceola will welcome children into their family. "It’s not lost on me that I’m 53. I will be the old dad, but so it goes," he said. "It could be a good thing. We’ll see."

Related: Jerry Seinfeld Cast Jon Hamm and John Slattery as Ad Execs in Unfrosted So He Could 'Finally Be in Mad Men'

<p>Axelle/Bauer-Griffin/FilmMagic</p> Jon Hamm (left) and Anna Osceola


Jon Hamm (left) and Anna Osceola

Hamm most recently caught up with PEOPLE in December 2023, when he dished on spending the holidays with Osceola some six months after they tied the knot.

“The best part of it is just being together. That's really it,” he said at the time. “And it's doubly nice that we're married now and that's really fun, but hopefully that continues on and you start creating new traditions with your family and all of those things, and that's the best.”

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