Landman's Jon Hamm Has A Sizable Age Gap With His Wife

Due to the major success of "Mad Men," Jon Hamm and his character Don Draper are forever linked. When Hamm's breakout role ended after seven seasons, it wasn't an easy transition. "It's a loss," Hamm admitted to ABC News in April 2015. "You go through the five steps of grief." It was a tumultuous time of endings and beginnings stacked on top of each other. Hamm and his longtime partner, Jennifer Westfeldt, broke up, and the groundwork was laid for his relationship with soon to be girlfriend Anna Osceola. Like Hamm, Osceola's an actor, and she made a guest appearance on the final episode of "Mad Men." However, their romance didn't begin right away, and it took until 2020 for them to go public with their relationship.

While it's likely Hamm needed time to heal after his previous 18-year relationship with Westfeldt, it's also possible that the age gap with Osceola could have caused a delay. Although other celebrity couples have bigger age differences than the 17 years between Hamm and Osceola, the "Landman" star has always felt he appears older than his biological age. "I was the guy who was 25 but looked 35," Hamm recalled to The Hollywood Reporter in June 2024. "I didn't look like I was in high school when I was in high school." Hamm felt his more mature looks hindered him at the beginning of his acting career. Happily, in his relationship with Osceola, it seems like it's not a big deal.

Jon Hamm and Anna Osceola also have a solid working relationship. They appeared in the 2022 movie "Confess, Fletch" (along with former "Mad Men" star John Slattery), and they're both part of the TV series "Your Friends & Neighbors." The couple has a relaxed on-set dynamic, and it's extra cozy when their dog joins them at work. Hamm and Osceola also have a shared attitude about preserving their privacy and eschewing social media, even for the purposes of prompting their onscreen endeavors.

While he previously claimed he wasn't one for a formal commitment, Hamm broke his rule and married Osceola in July 2023. "I hope it turns into kids," Hamm informed The Hollywood Reporter almost a year later. Then, in a brief nod to his age gap with Osceola, Hamm added, "It's not lost on me that I'm 53. I will be the old dad, but so it goes." Reportedly, he was interested in having children during his previous relationship thoughHamm never married Jennifer Westfeldt.

With age comes wisdom, and Hamm is taking advantage of his life experiences in his relationship with Osceola. "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,'" Hamm explained to Elle in April 2026.