Jon Hamm Had Doubts About Marriage Before Meeting Wife Anna Osceola

Jon Hamm didn't believe in marriage when he met his future wife Anna Osceola on the set of "Mad Men" in 2015. As People notes, though they have known each other since, it wasn't until summer of 2020 when the two reconnected and started dating officially. Appearing on Howard Stern's radio show in 2022, Hamm opened up about his new relationship. "This is all part of what I'm saying. This is another place in my life that I feel very settled and comfortable," he said, adding that he's "very much" in love with his girlfriend. "I'm in a relationship right now and it's comfortable." After nearly three years of keeping their romance low-key, Hamm popped the big question to Osceola sometime in February 2023. A source told Us Weekly that the proposal "happened a while back," but that Hamm and Osceola "are still on cloud nine" over their engagement. "They have so much fun together and already feel married," the insider noted.

Hamm and Osceola officially tied the knot on June 24, 2023. Per TMZ, they exchanged vows at the Anderson Canyon in Big Sur, California where the series finale of "Mad Men" was filmed. Several stars were in attendance to witness the big event, including Hamm's co-star John Slattery and Billy Crudup — who himself just got hitched to his longtime girlfriend Naomi Watts. Others were Paul Rudd and Tina Fey. Hamm explained why he was against the idea of marriage in an interview years before he met the love of his life.

Jon Hamm had sworn off the idea of marrying just a few years before meeting Anna Osceola. Speaking with Playboy in 2012 (via the Daily Mail), the "Mad Men" star said he doesn't believe in marriage and was uninterested in having his own children. "I don't have a driving force to have a baby," he said, admitting that his parents' failed marriage had contributed to his views. "I don't have a particularly defined example of marriage in my life. My parents got divorced when I was two and never remarried. So it doesn't mean anything to me," he explained.

At the time, Hamm was in a long-term relationship with actor and screenwriter Jennifer Westfeldt. The pair broke up in 2015 after 18 long years together. Regardless of what he thinks about marriage, Hamm said that he wasn't judging those who do find value in it. "I don't mean to say that it shouldn't mean things to other people," he said. "It's just my experience. I don't have that paragon of married life to look at and think, 'Oh yeah, that's it! That's what I want!” Interestingly, Westfeldt seemed to have mixed feelings about the whole thing when interviewed by the New York Times that same year. "I never thought I'd be this age and not have kids," she confessed. "I kept feeling like I'd wake up with absolute clarity, and I haven't. ... I may wake up tomorrow with that lightning bolt, and I'll have to scramble to make it happen."

In his chat with Howard Stern in 2022, Jon Hamm shared how meeting his wife Anna Osceola has changed everything he knew about love and marriage. Having tied the knot at 52 years old, the "Baby Driver" actor said it was only after he'd dated Osceola — and worked through his unresolved trauma and mental health — that he'd started to really think about his future. "It's only been in the last couple years of me kind of sitting down and really thinking about all that stuff that's made the relationship that I'm in now even more meaningful and opened up the possibility of things like being married, having kids," Hamm explained. "You know, defining a new version of happiness, life, wellness, all that stuff." He added, "It sounds hokey and whatever, but it's real."

Having previously been vocal about his wish not to get married, Hamm said that he now sees the true value of marriage. "Ideally, it gives you and your partner a sense of stability and comfort and an identifying capacity that is better, deeper, richer, than 'it's my girlfriend' or 'my boyfriend' or what have you," he said on the "Table for Two with Bruce Bozzi" podcast, ahead of their nuptials. "This is the exciting part of life, and it's a signpost and a signifier of the next chapter and phase," Hamm said, adding, "It's exciting because it's all potential, it's all possibility, and it's all positive."