Jon Hamm Wife Anna Osceola: From Mad Men Cameo to Big Sur Bride

If you’ve seen Jon Hamm in Mad Men, Top Gun: Maverick, or The Morning Show and then gone to Google “Jon Hamm wife,” you’re really asking how one of Hollywood’s most famously long-term bachelors finally ended up married. The answer is Anna Osceola – an actress with East Coast roots, a low-key public profile, and a love story with Hamm that quietly unfolded over years.

Who Is Jon Hamm’s Wife, Anna Osceola?

Jon Hamm’s wife, Anna Osceola, is an American actress born in Cambridge, Massachusetts, in April 1988. She grew up in New England and eventually made the move west to pursue acting, the slow, steady way rather than via some giant breakout moment.

Her career has mostly been built on television work. Over the years she’s appeared in shows like:

• Greek

• Rizzoli & Isles

• NCIS

• Law & Order: SVU

• Law & Order True Crime: The Menendez Murders

• Curb Your Enthusiasm

• Animal Control

On the film side, she’s had roles in projects like Superhero Movie and the 2022 crime-comedy Confess, Fletch, where she shared the screen with Hamm again.

Despite the Hollywood connection, Anna stays pretty low-profile. She’s not a big social-media personality, she doesn’t do many interviews, and she tends to show up only when it really makes sense – a premiere, a red carpet, or a project she’s actually in.

The First Meeting: Mad Men’s Final Episode

The seeds of their relationship go back to one of TV’s most talked-about finales.

In 2015, Anna appeared in the last episode of Mad Men. She played Clementine, the receptionist at the California retreat where Don Draper ends up during his late-series crisis and breakthrough. Those scenes were filmed on the cliffs of Big Sur, at a retreat-style location overlooking the Pacific.

That finale is generally understood as the first time Hamm and Osceola worked together and met properly. At that point, it was simply a professional encounter: he was closing out the role that made him a household name, and she was making a brief but memorable appearance in the show’s final hour.

There’s no real evidence they started dating back then; that connection seems to have grown much later. But it does mean their story started in a fictional retreat in Big Sur years before they said “I do” there in real life.

From Co-Workers to Couple

After Mad Men wrapped, both of them kept working. Hamm went on to projects like Baby Driver, Tag, Good Omens, and Top Gun: Maverick. Anna stayed busy with TV guest spots and other roles.

In 2015, Hamm’s long-term relationship with writer and actress Jennifer Westfeldt ended after nearly 18 years together. In the years that followed, he focused on getting sober, going to rehab, and doing a lot of personal work in therapy. He’s been pretty open about the fact that he needed that time to get his life in order and figure out what he really wanted.

Anna re-entered the picture publicly a few years later. In 2020, the two started appearing in candid photos together around Los Angeles – playing tennis, running errands, leaving cafes. It was the first sign that they were more than just former co-workers. From there, they slowly became a more regular sight as a couple at industry events and dinners, but always in that fairly relaxed, not-trying-too-hard way.

By 2022, they were working together again in the film Confess, Fletch, with Hamm in the lead and Osceola in a supporting role. By then it was clear: this wasn’t a fling, it was a real, long-term relationship.

Getting Engaged and Going Back to Big Sur

Reports of their engagement surfaced in early 2023. While they didn’t do a big joint statement, multiple reliable outlets confirmed that Hamm had proposed after several years of dating.

They chose a meaningful spot for the wedding: Anderson Canyon in Big Sur, California, the same coastal stretch used as the retreat setting in the Mad Men finale where they first met. The ceremony took place in late June 2023, with an outdoor setup overlooking the ocean, friends and family in attendance, and a very “California-romantic” vibe.

Photos from the day show Hamm in a classic tux and Anna in a strapless white gown, looking more like a couple who wanted a beautiful day with their people than a pair staging a media event. The symbolism wasn’t subtle: the place where Don Draper’s fictional story ended became the place where theirs, in a very real way, began a new chapter.

Later, in interviews, Hamm called the wedding “perfect” and admitted that the idea of proposing had actually scared him. Not because he doubted Anna, but because the seriousness of marriage felt huge. He’s said that leaning into that fear – instead of running from it – was part of why he felt ready this time.

What Married Life Looks Like for Them

Since getting married, Hamm has talked more openly about how much his life has shifted.

In recent interviews, when asked about his ideal day off, he doesn’t talk about parties or fancy trips. He mentions quiet days at home with Anna and their dog, cooking, watching TV, or traveling together when they can. It’s a marked contrast to the public image he once had as a hard-drinking, endlessly social leading man.

There’s a noticeable age gap – Anna is 17 years younger – but coverage from people who’ve worked with them tends to describe the relationship as an easy match: similar sense of humor, similar approach to keeping their private life private, and a shared comfort with not oversharing their relationship for attention.

He’s also said that being married gives him a sense of stability and comfort he didn’t have before, and that committing to Anna has opened up what he calls “a new version of happiness,” one that includes things he used to be afraid of, like the idea of having a family.

Do Jon Hamm and Anna Osceola Have Kids?

As of the most recent reliable information, Jon Hamm and Anna Osceola do not have children.

That said, Hamm has been candid about the fact that they’ve talked about starting a family. In interviews, he’s joked that he’s fully aware he’d be “the old dad” but that he’s open to it now in a way he wasn’t ten or fifteen years ago. For the moment, though, it’s still just the two of them (and the dog) figuring out married life.

Why This Marriage Feels Different

Another reason “jon hamm wife” keeps trending is the contrast with his past.

For almost two decades, Hamm was in a serious relationship with Jennifer Westfeldt. They lived together, made films together, and were considered one of Hollywood’s more stable long-term pairs, but they never married. After that relationship ended, he went through rehab and therapy and spent time rethinking what he wanted his life to look like.

With Anna, the energy is different. He’s talked about being more emotionally ready, less afraid of commitment, and more interested in building a home life than in keeping every option open. Marriage, kids, and long-term stability used to seem daunting; now he describes them as something “scary in a good way” – big, yes, but worth leaning into.