Jon Hamm Reveals Why He Changed His Mind About Marriage At 50

Jon Hamm is ready to settle down. 

Once dubbed Hollywood’s most eligible bachelor, the 51-year-old heartthrob reveals his true thoughts on commitment, marriage, and starting a family. For too long, the actor has been compared to his most famous character: Don Draper of Mad Men: a cavalier, womanizing drunk who only cared about his desires and little else. Even though Hamm was in a relationship for nearly 20 years with writer and actress Jennifer Westfeldt, people assumed he wasn’t fit for marriage or that his mind was elsewhere.

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Surely a handsome, attractive man like him wouldn’t want to tie himself down to a tiresome life of monogamy? Wouldn’t he want to continue sampling all the flavors in the market for as long as he could? 

In a candid interview with Howard Stern, the actor delves into why he’s kept away from the institution all these years and why he’s changed his mind as of late. As always, it’s not a straightforward journey, and Hamm had to account for a wide range of factors to come to this conclusion. 

His decision-making process unearths a beautiful story of choice, learning, and following one’s heart. 

Jon Hamm On Marriage, Children, and Taking The Plunge With His Girlfriend

Jon Hamm will be the first to tell you he’s resisted marriage for as long as he could. 

In 2010, while he was with Westfeldt, Hamm famously declared that he doesn’t have the “marriage chip.” He added that both he and Westfeldt didn’t have the greatest examples of marriage in their families, which is why they were apprehensive about exchanging vows. “But Jen is the love of my life, and we've already been together four times longer than my parents were married,” he said regarding Westfeldt. A few years later, in 2012, Hamm revealed his fatherhood aspirations or lack thereof. “I'd be a terrible father!” he told Us Weekly. At the time, he indicated that it was his intense work schedule that kept him from diving into parenthood. 

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Cut to ten years later, and Hamm has not only changed his stance but has been able to tap into his tender side. 

In September 2022, Hamm goes on The Howard Stern Show and speaks about where he stands regarding marriage and children, especially with respect to his age and current needs. In the clip, Stern asks him whether he could ever see himself committing to “one woman” for the rest of his life and then subsequently go through the motions of long-term partnership, marriage, the whole works. Hamm replies with a solid affirmative, adding that he’s “settled and comfortable” in his place in life. The Top Gun star also confirms he’s in a relationship at the moment and admires the feeling of being taken care of as well as caring for someone else. 

Though Hamm doesn’t mention her by name, his girlfriend in question is actress Anna Osceola. The two reportedly met on the set of Mad Men in 2015 but didn’t start dating until 2020, as confirmed by multiple media outlets. Since then, they’ve been spotted grabbing meals together, going on vacations, and playing tennis. They made their red carpet debut in March 2022 at an Oscars afterparty. 

The relationship seems to be thriving, as Hamm is contemplating spending the rest of his life with Osceola. But it’s not solely her magical arrival that’s caused him to rethink marriage; he’s also done tremendous work on his mental health and emotional processing over the years. “It's also been a process of working on myself, my mental health, all the stuff with my therapist,” he says. 

Jon Hamm's Stance On Marriage Was Shaped By A Childhood Tragedy

The St. Louis native lost his mother to colon cancer when he was only 10, a tragedy that led to profound grief and trauma throughout his adolescence. In fact, the pain was so thorough and consuming that it severed his ability to build and nurture connections with others, romantic or otherwise. “When you lose someone that's so important to you, like a mother, so early, that that creates a wound that blocks a lot of that emotional accessibility,” he tells Stern. As a result, it took until his late forties to realize the depth of his sadness and take the necessary measures to reclaim some of his “availability and vulnerability.”

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For starters, therapy played an enormous role in helping him bridge some of the gaps. He took the time to “sit down” and excavate the root of his suffering, getting to the bottom of what exactly held him back from sharing himself with others. Everyone’s experience with loss is different; how it surfaces and materializes always varies from person to person. In Hamm’s case, his anguish weighed down his relationships down, ridding them of any value or emotion. If you’re not in a position to accept happiness, why would you feel worthy of long-term commitment?

Thankfully, Hamm found the light at the end of the tunnel in recent years. “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, defining a new version of happiness, life, wellness,” said Hamm. He’s able to experience the little joys with Osceola and has even begun envisioning a future with her. “It sounds hokey and whatever, but it's real and it's — for want of a better word — it's what I'm working for,” he says. 

When Stern asks if Hamm is in love, the latter responds: “I very much so am.”

Hamm’s honesty carries a heartfelt insight about human nature: we’re often not aware of our own feelings and it takes time to unearth their genuine form. For example, Hamm thought he felt a certain way about marriage; he was firm in his position and was confident knowing where it came from. But, as it turns out, his reasoning was masking something far more traumatic and poignant — a force that he didn’t even know was prevailing over his actions. He wouldn’t have known about his hurt until he was forced to reckon with his internal workings, and that’s why he came to a brand-new conclusion about himself. Perhaps he is fit for marriage, perhaps he is fit to be a father; he just had to shift perspective and change his approach to human connection. 

What Jon Hamm Teaches Us About Knowing Ourselves

Hamm’s journey shouldn’t necessarily force us to change our stance on marriage and children. Indeed, those are some of the most consequential decisions of our life that we’ll ever make, and no one should be following the guidance of their peers, neighbors, or celebrities.

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However, what we should be cognizant of is the full extent of why we’re choosing to lean one way or the other. Are we fully aware of the consequences? Will we have any regrets? It’s crucial to take the time and unpack our motivations, and if, after our inspection, we still feel confident with our choice, nothing should get in our way. Live your life however you want to live it, but always know why. 

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