Jon Hamm and Anna Osceola Are Reportedly Expecting Their First Child Together

Actor Jon Hamm is reportedly preparing to become a father for the first time.

According to a report published by the Daily Mail on Monday, Aug. 10, Hamm's wife, Anna Osceola, 38, is expecting the couple's first child. The publication shared photos from a recent beach outing in the Hamptons, where Osceola appeared to reveal a noticeable baby bump. Earlier images taken during a trip to Ischia, Italy, in late June had also sparked speculation that the actress was pregnant.

The reported pregnancy marks a significant milestone for Hamm, who previously spoke openly about being uncertain whether he wanted to have children.

In a 2008 interview with The Guardian, while still in a long-term relationship with actress Jennifer Westfeldt, Hamm admitted he had mixed feelings about parenthood.

"I don't necessarily want kids," he said at the time, explaining that although many of his friends were starting families, he had not decided whether fatherhood was the right path for him.

Hamm and Westfeldt ended their nearly 20-year relationship in 2015. That same year, he met Osceola while filming the final season of Mad Men, where she made a brief appearance as a receptionist. The two did not begin dating until 2020.

By 2024, Hamm acknowledged that his perspective on life had evolved considerably.

Speaking to The Hollywood Reporter, he reflected on marrying Osceola in June 2023 during a ceremony held in Big Sur, California—the same location featured in the memorable finale of Mad Men.

The actor described the wedding as an emotional experience surrounded by family and close friends, calling it a fresh beginning and a meaningful new chapter in his life.

During the same interview, Hamm also revealed that starting a family had become an important goal despite being aware that he was entering fatherhood later in life.

"I hope it turns into kids. It's not lost on me that I'm 53," he said.

Today, Hamm and Osceola continue to share both their personal and professional lives. The couple currently appear together in Apple TV+'s Emmy Award-winning drama Your Friends & Neighbors, while reportedly preparing to welcome their first child together.