Jon Hamm to Become a First-Time Dad at 55

Jon Hamm is reportedly on his way to playing "old dad," just as he once predicted. A source tells People the 55-year-old actor and wife Anna Osceola, 38, are expecting their first child, though reps for the pair haven't commented. The two, who met through Mad Men and later costarred in Your Friends & Neighbors, married in June 2023 at Big Sur's Anderson Canyon, where the Mad Men finale was shot. They met while filming the 2015 finale, in which Osceola had a minor role as a receptionist at a health retreat, but they didn't become a couple until more than five years later, Page Six reports.

In past interviews, Hamm has said marriage and the possibility of kids became more appealing after he felt "settled" with Osceola. "It's been great," he told the Hollywood Reporter in 2024. "And I hope it turns into kids. 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." In April, he told People that it had been fun to work with Osceola in season 2 of Your Friends and Neighbors. He joked that one perk was not having to "have an hour long conversation on what I did at work."