Jon Hamm Marries Former ‘Mad Men’ Costar Anna Osceola: Inside Their Plans on ‘Starting a Family’

They looked, well, perfect. Standing atop the edge of a cliff before sunset, the Pacific Ocean crashing on the rocks below, Jon Hamm and his former Mad Men costar Anna Osceola made it official. 

“The setting and the ceremony were lovely,” one guest tells In Touch. “Jon couldn’t have looked happier, and his bride was beaming.”

Jon met Anna eight years ago when she played the receptionist at the hippie retreat that his character, ad executive Don Draper, visited before creating an iconic commercial on the 2015 series finale of the Emmy-winning series Mad Men. It was a full-circle moment for Jon and Anna, who chose the same location — Anderson Canyon in Big Sur, California — as the site of their nuptials, which were attended by famous friends John Slattery, Brooke Shields, Paul Rudd, Tina Fey, Billy Crudup, Larry David and more.

“Jon’s pals never thought they’d see this day, him standing at the altar, but never say never,” a source says. 

Years of therapy and hard work brought him to this place. In 2012, the actor — who was in an 18-year relationship with screenwriter and actress Jennifer Westfeldt at the time — famously said he had no aspirations to become a husband or plants to have kids. His parents divorced when he was 2, leaving him without “a particularly defined example of marriage,” in his life, he admitted. He then lost his mother to colon cancer when he was 10; his father died 10 years later. 

Then, in 2022, Jon confessed his views on marriage — and having kids — had changed. 

“It’s been a process of working on myself, my mental health, with a therapist, unpacking all of that trauma” that blocked “a lot of that emotional accessibility, availability and vulnerability,” he previously confided. “It’s only been in the last couple of years of me sitting down and really thinking about all that stuff” that made his romanic relationship with Anna — which began in 2020 — “even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness, all that stuff.” 

His wedding day made him even more sure of everything. 

“Watching Anna walk down the aisle really moved him,” a wedding guest tells In Touch. “Jon looked at her with such love. It made him proud to be taking this journey with a woman he considers his true partner.” 

Jon is glad that he opened himself up. 

“Jon has embraced the commitment of it all and is now looking forward to starting a family with Anna,” a source says. 

The actor hinted as much in a recent interview, saying the future is “exciting. It’s exciting because it’s all potential, it’s all possibility and it’s all positive.”