Landman Star Jon Hamm Has A Sizable Age Gap With His Real-Life Wife

While age-gap relationships are not the most favorable dynamic for public optics, they remain commonplace in Hollywood. Countless stars end up walking down the aisle with someone much younger than themselves, whether as a result of physical attraction, a desire to stay young, or simply finding a soulmate who happens to be much younger. This is especially true for "Mad Men" and "Landman" star Jon Hamm, who tied the knot with Anna Osceola in June 2023, despite their staggering age gap of 17 years; Hamm was born in 1971, while Osceola was born in 1988.

The acting couple first met on the set of "Mad Men" in 2015, the same year Hamm had a high-profile breakup with his partner of 18 years, actor and director Jennifer Westfeldt. Osceola played only a minor role in the series finale. With both his long-term relationship and "Mad Men" ending in 2015, Hamm reportedly spiraled into depression and entered rehab. After some self-care, he and Osceola reconnected five years later and began a romantic relationship in 2020. In 2022, they acted together once more in the remake "Confess, Fletch." The next year, they were married at a former "Mad Men" location in Big Sur, California, with many celebrities in attendance.

The "Landman" cast and their real-life partners have been a hot topic of conversation since the show first aired in November 2024, from Billy Bob Thornton's sixth wife Connie Angland to James Jordan's 2025 engagement. Hamm's marriage is no exception, with their age gap proving to be controversial among fans. "Another 50 something man with a woman who could be his daughter. Great," an Instagram user commented on a video of Hamm and Osceola being spotted together in New York City. "Oh, he brought his daughter how nice. Lol," another user joked. 

Jon Hamm had doubts about marriage before meeting Anna Osceola, who is 17 years his junior. He had an 18-year-long relationship with fellow actor Jennifer Westfeldt that began in 1997, even working together in the films "Kissing Jessica Stein," "Ira & Abby," and "Friends with Kids." In 2010, Hamm told Parade that Westfeldt was the love of his life. "I don't have the marriage chip, and neither of us have the greatest examples of marriage in our families. But Jen is the love of my life, and we've already been together four times longer than my parents were married." Despite this previous confession, the Hollywood power couple called it quits in 2015 as his hit show "Mad Men" was wrapping up. That same year, Hamm went to rehab for 30 days while battling depression.

After spending years working on himself, Hamm tackled his hesitancy to get married and discovered ways to make it work in his relationship with Anna Osceola. "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," Hamm told Elle in April 2026. "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."