Jon Hamm, 55, expecting first child with wife Anna Osceola, 38, as she debuts baby bump

Jon Hamm is expecting his first child with his wife Anna Osceola, who debuted her baby bump while the couple were at the beach.

The couple, who met on the final season of Mad Men, were spotted enjoying the sun and surf in the Hamptons last week.

The 38-year-old actress wore a green bikini as she showed off her growing baby bump, while her husband Hamm, 55, went shirtless after a dip in the sea.

The couple tied the knot in 2023, in a lavish wedding ceremony at the location where the couple’s characters first met in the hit Madison Avenue advertising drama, and where the show infamously wrapped up its seven-season run.

In that final 2015 episode, Hamm’s character Don Draper visits a spiritual retreat and – depending on your read of the last scene – either experienced a moment of personal enlightenment or thought up the 1971 ‘Hilltop’ advert for Coca-Cola.

His character briefly shared a scene with Osceola’s, who was a receptionist at the retreat in question. 

The couple wed in an outdoor ceremony at Anderson Canyon in Big Sur, with attendees reportedly including Billy Crudup, Tina Fey and Paul Rudd.

Hamm and Osceola made their red carpet debut together at an Oscars afterparty in 2022, seven years after meeting while filming that finale episode and two years after being romantically linked.

Hamm had previously indicated he might not want children while in a long-term relationship with actor and screenwriter Jennifer Westfeldt. The former couple co-starred in several productions, including the 2011 film Friends with Kids.

Hamm 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.’

Hamm and Westfeldt were together from 1997 to 2015 and never married. 

Speaking to the New York Post in 2008, Hamm said of their relationship: ‘We may not have a piece of paper that says we’re husband and wife, but after 10 years, Jennifer is more than just a girlfriend. What we have is much deeper and we both know that.

‘To me, people get married when they’re ready to have kids, which I’m not ruling out.’

Metro contacted Jon Hamm’s representatives for comment on this story.