Jon Hamm is thrilled to embrace fatherhood as his wife, Anna Osceola, is expecting their first child. However, this wasn’t always part of his life plan.
“Jon was in a very different mindset and a different place in his life when it came to having kids in the past,” a source exclusively tells Us.
The insider reveals that “years ago” Hamm, now 55, had different feelings about becoming a father.
The Mad Men alum’s outlook has evolved considerably since then, according to the source, noting that Hamm is now in a completely different stage of life.
Hamm’s attitude towards having children shifted significantly after Osceola, 38, became a part of his life.
“Anna has always known that she wanted to have a family, but she was incredibly understanding of where Jon was when they first started dating,” the source tells Us.
The insider explains that the topic of becoming parents was never something Osceola pressured Hamm about when they first started dating in 2017, after meeting during the final season of Mad Men in 2015. Osceola played Clementine, a receptionist at the spiritual retreat visited by Hamm’s character, Don Draper. Us confirmed in June 2020 that Hamm and Osceola were officially dating.
“They were very open with each other from the beginning about what they both wanted and how they were feeling,” the source shares, describing the topic as “an ongoing conversation.”
Anna Osceola and Jon Hamm. Amy Sussman/Getty Images for Vanity Fair
As their relationship blossomed, both Hamm and Osceola reached a point where they felt ready to take the next step.
“They’re both so excited and it really feels like the right time for them,” the source tells Us, adding that Hamm “is in a place in his life where he’s ready and genuinely excited to become a dad.”
Us has reached out to Hamm and Osceola’s representatives for comment.
Before meeting Osceola, Hamm was in a long-term relationship with Jennifer Westfeldt, which lasted from 1997 to 2015.
Jon Hamm and Anna Osceola are excited about expanding their family with their first child 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 […]
Hamm shared his thoughts on parenthood with Us in March 2012, saying, “I see my friends who have children and I’m like, ‘Dude, how are you even upright, much less here at work at 6 a.m.?'”
After his breakup with Westfeldt, 56, in September 2015, Hamm began a relationship with Osceola, whom he married in June 2023.
About a year after their wedding, Hamm hinted at his newfound openness to having children. In an interview with The Hollywood Reporter in June 2024, he expressed his willingness to embark on the journey of parenthood with Osceola.
“I hope it turns into kids,” Hamm said, acknowledging his age, “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.”
News surfaced on Monday, August 10, that Hamm and Osceola are expecting their first child together after the actress was seen with a noticeable baby bump while in a bikini.
“Jon has always wanted to be a dad with Anna,” a source exclusively informed Us on Monday, adding that Hamm is “over the moon” about the prospect of fatherhood.
The insider mentioned that Osceola is “pretty far along now and feeling really good” as she prepares for the new addition. “They have been trying to relax a bit but are enjoying making plans for the baby.”
