Jon Hamm is set to become a father for the first time at 55. Exclusive pictures obtained by the Daily Mail show his wife, Anna Osceola, 38, is expecting their first child.
The couple, who married in 2023, were spotted enjoying a beach day in the Hamptons, with Osceola flaunting her blossoming baby bump in a dark green bikini.
The actress, who appears to be in her second trimester, glowed in the two-piece as she took a quick dip in the ocean. A shirtless Hamm looked giddy as he doted on his pregnant wife during a break in his hectic schedule.
In June, the couple vacationed at a luxury resort in Ischia, Italy. The Daily Mail has contacted representatives for Hamm for comment.
A surprise turnaround
The couple's baby joy marks a surprise turnaround for Hamm, who once said he didn't "necessarily want kids" while with his long-term partner Jennifer Westfeldt. He told The Guardian in 2008: "I don't necessarily want kids. A lot of our friends are having children and I don't know if it's for me. I haven't come down hardcore on either side of the argument. I think when people come from a stable family having children becomes a celebration and I'm not sure it would be that way for me."
How Hamm met Osceola
Hamm's relationship with Westfeldt began in 1997 and lasted nearly two decades before the pair separated in 2015. He first met Osceola that same year, when she appeared in one episode of Mad Men as a receptionist. Just months later, Hamm and Westfeldt announced they had ended their relationship.
A source told the outlet at the time that Hamm's "party-heavy lifestyle" had become too much for Westfeldt, and that she wanted him "to grow up" but "he never wanted to." Hamm was later spotted with Osceola in 2017, and the pair were confirmed to be dating in 2020.
Engagement and marriage
Hamm and Osceola made their red carpet debut in 2022 and appeared together in the crime comedy Confess, Fletch. They became engaged in February 2023, with a source telling Us Weekly about the new step in their relationship. Hamm later discussed his romance on The Howard Stern Show, saying it made him reevaluate his love life up to that point.
Mad Men changed Hamm's life in more ways than one. Not only did the show launch his career, it also brought his future wife into his life.
From no marriage chip to family man
In 2010, while still dating Westfeldt, Hamm said neither of them had any interest in marriage. He told Parade: "I don't have the marriage chip, and neither of us have the greatest examples of marriages in our families."
But in a 2022 interview with Sirius XM, Hamm said everything changed once Osceola entered his life. He credited her with inspiring him to seek therapy for the trauma he endured as a child after losing his mother to colon cancer at age ten, saying it gave him a newfound drive to become a family man.
"[I'm in] another place in my life where I feel very settled and comfortable. I'm in a relationship right now and it's comfortable," he said, adding that getting professional help "opened up the possibility of things like being married and having kids."
"I've been really thinking about all that stuff, that's made the relationship that I'm in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness," he continued. "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?"
Hoping for kids
In a June 2024 interview, Hamm said he hoped his marriage would produce children. He said: "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, but so it goes. It could be a good thing. We'll see."
