Jon Hamm’s Change of Heart on Parenthood with Anna Osceola
Jon Hamm is “truly thrilled” about becoming a father, now that his wife Anna Osceola is expecting — though he didn’t always envision having children.
“Jon was in a very different mindset and a different stage in his life regarding kids in the past,” a source tells Us exclusively.
The insider shares that “years ago,” Hamm, 55, “had a different outlook on whether fatherhood was what he desired for himself.”
The Mad Men star’s “perspective has evolved significantly since then,” the source continues, noting that Hamm is now in a “completely different place in his life.”
Hamm’s willingness to embrace fatherhood has seemingly changed since Osceola, 38, came into his life.
“Anna has always known she wanted a family, but she was incredibly understanding of Jon’s feelings when they started dating,” the source tells Us.
The insider explains that Osceola “never pressured” Hamm into parenthood when they initially became romantically involved in 2017 after meeting during the final season of Mad Men in 2015. Osceola portrayed Clementine, a receptionist at the spiritual retreat his character, Don Draper, visited. (Us confirmed in June 2020 that Hamm and Osceola were officially an item.)
“They communicated openly from the start about their desires and feelings,” the source reveals, calling the subject “an ongoing dialogue.”
As their relationship deepened and their connection grew stronger, the insider notes that Hamm and Osceola “reached a point where they were both ready to take that next step.”
“They’re both super excited, and it genuinely feels like the perfect time for them,” the source tells Us, adding that Hamm “is in a good place in his life and is genuinely thrilled about becoming a dad.”
Us has reached out to Hamm and Osceola’s representatives for comment.
Before meeting Osceola, Hamm was in a relationship with Jennifer Westfeldt for 18 years, from 1997 to 2015.
Hamm spoke to Us about his views on parenthood back in March 2012, admitting at the time, “I see my friends who have kids, and I’m like, ‘Dude, how are you even upright, not to mention here at work at 6 a.m.?’”
After splitting from Westfeldt, 56, in September 2015, Hamm began dating Osceola, whom he married in June 2023.
A year after their marriage, Hamm hinted that his stance on having children had shifted. He told The Hollywood Reporter in June 2024 that he was open to becoming a first-time dad and embracing that experience with Osceola.
“I hope it leads to kids,” Hamm remarked at the time. “I realize I’m 53. I’ll be the older dad, but that’s okay. It could be beneficial. We’ll see.”
On Monday, August 10, news broke that Hamm and Osceola are expecting their first child together after the actress was spotted in a bikini, highlighting her growing baby bump.
“Jon has always wanted to be a dad with Anna,” a source told Us on Monday, noting that Hamm is “over the moon” about the news.
The insider added that Osceola is “well along in her pregnancy and feeling great,” while they are getting ready for the baby. “They’ve been trying to take it easy but are enjoying planning for the little one.”
