Why Jon Hamm Changed His Mind About Having Kids Since He Met Wife Anna Osceola (Exclusive)

As their relationship evolved and their bond strengthened, the insider says that Hamm and Osceola “got to a place together where they both felt ready to take that 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 reps for comment.

Prior to meeting Osceola, Hamm dated Jennifer Westfeldt for 18 years from 1997 to 2015.

Hamm exclusively told Us his thoughts about parenthood in March 2012, sharing at the time, “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.?’”

Following his split from Westfeldt, 56, in September 2015, Hamm moved on with Osceola, whom he wed in June 2023.

One year after Hamm and Osceola got married, the actor hinted that he had a change of heart when it came to having kids. Hamm told The Hollywood Reporter in June 2024 that he was open to being a first-time dad and embarking on that journey with Osceola.

“I hope it turns into kids,” Hamm said at the time. “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 broke on Monday, August 10, that Hamm and Osceola are expecting their first baby together after the actress was photographed wearing a bikini that showed off her growing baby bump.

“Jon has always wanted to be a dad with Anna,” a source exclusively told Us on Monday, noting that Hamm is “over the moon” about becoming a father.

The insider added that Osceola is “pretty far along now and feeling really good” while getting into nesting mode. “They have been trying to relax a bit but are enjoying making plans for the baby.”