All About Anna Osceola, Jon Hamm’s Wife

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THE RUNDOWN

• Anna Osceola is best known for her work across television and her role in Confess, Fletch.
• She met Jon Hamm on Mad Men, but their relationship didn’t turn romantic until 2020.
• Hamm and Osceola married in 2023 and are now expecting their first child together.

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Jon Hamm and his wife, Anna Osceola, first crossed paths on the set of Mad Men in 2015, but their relationship didn’t turn romantic until years later. By 2020, they were spotted spending time together in Los Angeles, and over the next few years, their relationship unfolded mostly out of the public eye—until their June 2023 wedding in Big Sur, California.

Along the way, Hamm has offered rare glimpses into their relationship, describing marriage as an “exciting” new chapter and speaking candidly about what it means to build a life together. In August 2026, the couple reached another milestone when news broke that they are expecting their first child.

Here’s everything to know about Osceola and her relationship with Hamm.

She’s an actress.

Osceola grew up in Cambridge, Massachusetts, before moving to California to pursue acting.

She made her on-screen debut in 2007 in the TV movie Not Another High School Show. Over the years, she has built a steady résumé of television roles, including appearances on Greek, Rizzoli & Isles, NCIS, Law & Order: Special Victims Unit, and Law & Order True Crime.

She met Hamm on the set of Mad Men.

Osceola and Hamm reportedly first met in 2015 while filming the final episode of Mad Men.

Osceola had a small role in the series finale, playing a receptionist at a California retreat where Hamm’s character, Don Draper, ends up in the show’s final moments.

Although they met then, their relationship didn’t become romantic until years later.

They started dating in 2020.

The two were first romantically linked in 2020 after being photographed together on multiple outings in Los Angeles.

Photos from that time show the pair grabbing meals, playing tennis, and spending time together during the early months of the pandemic.

They made their red carpet debut in 2022.

After roughly two years of dating, Osceola and Hamm posed together at their first event in March 2022: the Vanity Fair Oscar Party.

They’ve since appeared together at events including the 2025 Academy Museum Gala and the 2026 Vanity Fair Oscar Party.

They got engaged in February 2023.

People confirmed Hamm and Osceola got engaged in February 2023.

Around that time, Hamm spoke about their romance during an appearance on The Howard Stern Show, saying, “I’m in a relationship right now and…it’s comfortable, it’s a feeling of taking care of someone else and being taken care of.”

When asked if he was in love, he said, “I very much so am.”

Hamm later reflected on the proposal in a June 2024 interview with The Hollywood Reporter, saying, “I just remember feeling, ‘This is really scary.’ Then going, ‘Well, it probably means it’s worthwhile.’”

In June 2023, they got married in Big Sur.

The couple tied the knot on June 24, 2023, at Anderson Canyon in Big Sur, California.

The location held personal significance—it’s near where the Mad Men series finale was filmed.

Hamm later reflected on the day during an appearance on Jimmy Kimmel Live!, saying, “It was very exciting….It was a perfect day. It was very sparsely attended, by our decision; it was small. And man, it was great.”

Before the wedding, he also shared his perspective on marriage during an appearance on the Table for Two podcast.

“Ideally, [marriage] 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.

The couple has worked together on-screen.

Osceola and Hamm reunited professionally in the 2022 film Confess, Fletch, where Hamm plays the lead role and Osceola appears in a supporting part.

They worked together again on the Your Friends & Neighbors TV series, with Osceola playing Maggie Haber alongside Hamm’s Andrew “Coop” Cooper.

Hamm spoke about having his wife on set during a March 2026 interview with Extra. “Having Anna around is great. She’s wonderful,” he said. “It’s great to go to work together….We can hang out. It’s nice to have somebody to eat lunch with and do scenes with. It’s a family affair, it’s really nice.”

A month later, he shared more about the experience with People. “It was great to have my wife, Anna, come in and be a part of it,” he said. “We get to bring the dog in as well sometimes, so that’s nice. We save money on dog sitting.”

Neither Osceola nor Hamm has social media accounts.

Both Osceola and Hamm maintain a low profile and do not have public social media accounts.

Hamm has spoken openly about his views on social media, telling InStyle in 2017, “The point of life is not to put dog ears on yourself and post it online for everyone to see.”

He added, “It’s fun, it’s adorable, but it’s the visual equivalent of masturbating—there’s no point other than immediate gratification.”

She’s influenced his music taste.

Osceola has also shaped some of Hamm’s offscreen interests. During a February 2026 interview clip shared by Entertainment Tonight following the Super Bowl, Hamm’s Your Friends & Neighbors co-star Olivia Munn said, “It’s his wife actually who got him into [Bad Bunny]. Anna was in Puerto Rico at a little bar or club and heard him way back when and has followed him since then, so she really got Jon into it.”

In April 2026, Hamm opened up about what marriage has taught him.

In an April 2026 interview with ELLE, Hamm reflected on the work that goes into maintaining a marriage.

“It’s a new set of skills, mostly communication,” he said. “Having come out of a long relationship that was not a marriage, then being single and figuring out life in my late 40s, and then being in a relationship again and what that all means—compromise and communication and all the things that you have to relearn, or reteach yourself—it doesn’t come overnight.”

He continued, “It’s a practice that you have to get better at. It doesn’t come without mistakes and failures, but it’s based on love and a willingness to say, ‘I’ve gotta be able to do better than this, so I need to figure out how I’ve been less-than and work on it.’ And that’s going to therapy and couples therapy, asking, ‘Is it me, is it them, or is it us?’ And it gets better.”

They’re expecting their first child.

On Aug. 10, 2026, People reported that Osceola and Hamm are expecting their first child together.

Two days later, a source spoke to the outlet about how Hamm feels about the impending milestone. “Jon’s incredibly excited,” the insider said. “This is something he and Anna have wanted and hoped for. He’s not thinking about his age or what anyone else has to say about it. He’s just really happy.”

Overall, “he’s happy, settled and ready for this,” the source added. “Anna’s amazing, and he feels very lucky that he gets to start a family with her.”

Hamm had previously spoken about the possibility of becoming a father. In a June 2024 interview with The Hollywood Reporter, he said, “It’s not lost on me that I’m 53. I will be the old dad, but so it goes. It could be a good thing. We’ll see.”