Jon Hamm, 55, is preparing to become a father for the first time, as his wife, Anna Osceola, 38, is pregnant with their first child. Osceola was recently photographed showcasing a visible baby bump during a beach outing in the Hamptons with the actor.

The actress, who appears to be in her second trimester, wore a green bikini, displaying her pregnancy during a beach day. Hamm was also present, seen doting on his wife.

The couple's pregnancy news first came to light in late June, when an onlooker spotted them at a resort in Ischia, Italy, where Osceola's baby bump was noticeable. A representative for Hamm has been contacted for comment.

This news marks a shift for Hamm, who had previously expressed doubts about fatherhood. In a 2008 interview with The Guardian, while in a long-term relationship with Jennifer Westfeldt, Hamm stated, "I don't necessarily want kids. A lot of our friends are having children and I don't know if it's for me." He elaborated that while he hadn't definitively decided against having children, he questioned if it would be a celebration for him, given his own family background.

Hamm and Westfeldt were together for 18 years, separating in 2015. Hamm first met Osceola in 2015 when she guest-starred on an episode of "Mad Men" as a receptionist. Shortly after their meeting, Hamm and Westfeldt announced their breakup.

Reports at the time suggested that Westfeldt found Hamm's "party-heavy lifestyle" difficult to manage and desired him to mature, which he was reportedly unwilling to do. Hamm and Osceola were first spotted together in 2017, and their relationship was confirmed in 2020.

The couple made their first red carpet appearance together in 2022 and also appeared in the crime comedy "Confess, Fletch." They announced their engagement in February 2023.

Hamm has spoken about how his relationship with Osceola prompted a reevaluation of his life and aspirations. In a 2022 interview, he revealed that he had begun therapy to address childhood trauma stemming from the loss of his mother at age 10. He credited this process with opening up the possibility of marriage and children.

"It sounds hokey and whatever, but it's real and for one of a better word, it's what I'm working for. What else is there other than that?" Hamm said about finding a new definition of happiness and wellness.

In a June 2024 interview, Hamm expressed his hopes for starting a family with Osceola. "It's been great. And I hope it turns into kids. It's not lost on me that I'm 53. I will be the old dad," he stated.