Inside Jon Hamm and Wife Anna Osceola’s Decision to Start a Family Amid Pregnancy News (Exclusive)

Jon Hamm and wife Anna Osceola are excited to expand their family with their first baby after three years of marriage.

“Jon has always wanted to be a dad with Anna,” a source exclusively tells Us. “Having a family was something that was really important to both of them from the beginning. They’ve talked about this chapter for a long time and were always on the same page about wanting children, so for it to actually be happening now feels incredibly special.”

The insider adds that Hamm, 55, is “over the moon” to become a dad. The actor has been “so attentive and excited about every little milestone” during Osceola’s pregnancy.

“Anna is pretty far along now and feeling really good,” the source says, revealing Osceola has been in nesting mode. “She took it easy at first and tried to stay under the radar. They have been trying to relax a bit but are enjoying making plans for the baby.”

Both Hamm and Osceola, 38, are very thrilled about this new relationship milestone.

“They’re both soaking it all in and are just so excited to become parents,” the insider continues. “Their relationship has only gotten stronger, and they feel really lucky to be going through this together.”

Us has reached out to Hamm and Osceola’s spokespersons for comment.

News broke on Monday, August 10, that Osceola is pregnant with her and Hamm’s first baby. According to photos obtained by the Daily Mail, the actress showed off a growing baby bump while wearing a bikini during a recent getaway to the Hamptons with the Your Friends & Neighbors star.

Hamm and Osceola met in 2015 while working together on Mad Men. Hamm starred as the iconic Don Draper since the inaugural premiere in 2007 while Osceola joined the series in its final season to play receptionist Clementine. The couple’s connection turned romantic in 2017.

“It’s only been in the last couple of years of me kind of sitting down and really thinking about all that stuff that’s made the relationship that I’m in now, is even more meaningful,” Hamm said of his and Osceola’s relationship in a September 2022 interview with Howard Stern. “And opened up the possibility of being married, having kids, defining a new version of happiness, life, wellness. All that stuff, it sounds hokey and whatever, but it’s real.”

Us confirmed that Osceola and Hamm got engaged in February 2023 and they wed that summer. One year later, Hamm shared his hopes to one day become a dad.

“I hope it turns into kids,” he told The Hollywood Reporter in June 2024. “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.”