Jon Hamm is reportedly preparing to become a father for the first time. The 55-year-old actor and his wife, Anna Osceola, 38, are expecting their first child, the Daily Mail reported Monday, Aug. 10. People also confirmed the pregnancy update through a source close to the couple.
Anna Osceola’s Baby Bump Appears in Hamptons Photos
GettyThe outlet published photographs of Osceola wearing a bikini during a beach day with Hamm in the Hamptons last week. Her growing baby bump was visible as the pair relaxed by the water.
The couple had previously been photographed together in Ischia, Italy, in late June, when Osceola also appeared pregnant. The famously private pair have not announced a due date or shared other details about the reported pregnancy.
Jon Hamm Once Questioned Whether Fatherhood Was for Him
Apple TVFor Hamm, the prospect of becoming a parent represents a notable change from the future he once pictured.
During a 2008 interview with The Guardian, while he was still dating Jennifer Westfeldt, Hamm acknowledged that he had not decided whether children were part of his plans.
“I don’t necessarily want kids,” he said. “A lot of our friends are having children, and I don’t know if it’s for me.”
Hamm connected some of that uncertainty to his childhood.
His parents divorced when he was 2, his mother died when he was 1,0 and his father died a decade later. Without the example of a stable family of his own, he said he was unsure whether parenthood would feel celebratory to him.
Hamm and Westfeldt ended their relationship in 2015 after 18 years together, as reported by The Guardian.
Jon Hamm Later Opened His Heart to Marriage and Children
GettyHamm’s outlook shifted as he worked through the loss and instability that shaped his early life. During a 2022 appearance on “The Howard Stern Show”, he said reflection had opened him to marriage, children and a different version of happiness.
After marrying Osceola, fatherhood began to feel less hypothetical.
“So, it’s been great. And I hope it turns into kids. It’s not lost on me that I’m 53,” Hamm told The Hollywood Reporter in 2024.
The Emmy winner recognized that he would be starting parenthood later than many people. He jokingly described himself as the “old dad,” but said the timing could prove to be a good thing.
Jon Hamm and Anna Osceola Met During the ‘Mad Men’ Finale
GettyHamm and Osceola first crossed paths in 2015 when she appeared in the “Mad Men” series finale. She played a receptionist at the California retreat visited by Hamm’s character, Don Draper.
They were first romantically linked in 2020 and became engaged in February 2023. The couple married on June 24, 2023, at Anderson Canyon in Big Sur, California, where the “Mad Men” finale was filmed, as per People.
Their lives have continued to overlap on screen. Osceola plays Maggie Haber in the second season of Hamm’s Apple TV series “Your Friends & Neighbors”, which stars him as troubled financier Andrew “Coop” Cooper.
Now, more than a decade after meeting on television, the couple is reportedly preparing to begin its biggest chapter away from the cameras.
The couple had not publicly confirmed the news of pregnancy.
