By Daily Mail (U.S.) | Created at 2026-08-10 19:58:24 | Updated at 2026-08-10 22:08:35
4 hours ago
Jon Hamm is set to become a first-time father at 55 as his wife, Anna Osceola, is pregnant.
The 38-year-old actress proudly showed off her baby bump in a bikini in the Hamptons with the Mad Men star last week, according to exclusive pictures obtained by the Daily Mail.
Osceola, who appears to be in her second trimester, glowed in a green two-piece as she took a quick dip at the beach.
A shirtless Hamm, who wed Osceola in 2023 after previously declaring he lacked the 'marriage chip,' looked giddy as he doted on his pregnant wife during a break in his hectic schedule.
In June, the couple vacationed at a luxurious resort in Ischia, Italy.
The Daily Mail has contacted representatives for Hamm for comment.
Actress Anna Osceola, who is married to Jon Hamm, showed off her baby bump in a bikini in the Hamptons last week, according to exclusive pictures obtained by the Daily Mail
The Mad Men star, 55, with his 38-year-old wife at the beach in New York
The couple's baby joy comes as a surprise turnaround for the actor, who previously openly said he didn't 'necessarily want kids' while he was still with long-term partner Jennifer Westfeldt. Above, the exes in 2015, the year they split after 18 years together
The couple's baby joy comes as a surprise turnaround for the actor, who previously openly said he didn't 'necessarily want kids.'
Hamm told The Guardian in 2008 while he was still with long-term partner Jennifer Westfeldt: '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.'
The actor was previously in a relationship with Westfeldt that began in 1997 and lasted nearly two decades before they separated in 2015.
Hamm first met Osceola in 2015 when she appeared in one episode of the popular AMC show as a receptionist. Just months later, Hamm and Westfeldt announced they had ended their longtime relationship.
Osceola, who appears to be in her second trimester, glowed in a green two-piece as she took a quick dip
Father-to-be Don Draper star Hamm showed off his buff frame on the sand in New York
Osceola looked glowing as she displayed her bump in the Hamptons
The soon-to-be parents enjoyed a relaxed day ahead of their firstborn's arrival
Osceola looked incredible as she relaxed at the beach
The couple were enjoying a weekend of leisure before the birth
Hamm met Osceola in 2015 when she appeared in one episode of the popular AMC show as a receptionist
At the time, a source told the outlet that Hamm's 'party-heavy lifestyle' had become too much for Westfeldt. Additionally, it was claimed Westfeldt wanted him 'to grow up' but 'he never wanted to.'
The Baby Driver actor was subsequently spotted with Osceola in 2017, and they were confirmed to have been dating in 2020.
Hamm and Osceola made their red carpet debut in 2022, and they also appeared alongside one another in the crime comedy feature Confess, Fletch.
The happy couple was confirmed to have become engaged in February 2023, and a source opened up to Us Weekly about the new step in their relationship.
Hamm previously discussed his romance during an interview on The Howard Stern Show, where he expressed that his relationship with Osceola made him reevaluate his love life up to that point.
The show Mad Men changed Hamm's life in many ways. Not only did it propel him into the spotlight and help launch a major career for the actor, but it also brought his future wife into his life.
In 2010, while Hamm was still dating Westfeldt, he first revealed that neither he nor his girlfriend had any interest in tying the knot.
'I don't have the marriage chip, and neither of us have the greatest examples of marriages in our families,' he told Parade.
Hamm previously admitted that he had no interest in ever walking down the aisle, but in a 2022 interview with Sirius XM, he revealed that everything had changed once Osceola came into his life.
He credited her with inspiring him to get therapy for the trauma he endured as a child following the death of his mother – which ultimately 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.
The star added that he recently became focused on improving his mental health and substance abuse issues through therapy – after spending years struggling with the trauma he faced as a child, after losing his mother to colon cancer at age ten.
He said getting professional help 'opened up the possibility of things like being married and having kids.'
Hamm previously revealed that he hoped his marriage would lead to children. He said in 2024, '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'
'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 at the time.
'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?'
In a June 2024 interview, Hamm revealed 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.'
