Hamm's Surprise Vows: Jon Hamm and Anna Osceola's Sunset Cliffside Wedding
Standing against the backdrop of a breathtaking cliffside and the rhythmic Pacific waves, Jon Hamm and former Mad Men co-star Anna Osceola declared their commitment to each other. As one guest narrated to In Touch, "The setting and the ceremony were lovely. Jon couldn't have looked happier, and his bride was beaming."
Hamm, 52, first met Osceola, 35, eight years ago on the set of Mad Men, where she portrayed the receptionist at a retreat visited by his character, Don Draper. Their nuptial venue, Anderson Canyon in Big Sur, California, echoed their professional past, as it was the same location featured in the show's series finale. The event, attended by famous faces like John Slattery, Brooke Shields, Paul Rudd, Tina Fey, Billy Crudup, Larry David, among others, came as a surprise to many of Hamm's friends. A source confessed, "Jon's pals never thought they'd see this day, him standing at the altar."
Indeed, Hamm's journey to the altar was marked by self-discovery and therapeutic intervention. In 2012, during his 18-year relationship with actress and screenwriter Jennifer Westfeldt, Hamm publicly renounced the idea of marriage and children. His early life experiences, including the divorce of his parents when he was 2 and the subsequent loss of both parents to cancer, left him without a solid model of marriage.
However, Hamm's viewpoint on matrimony and parenthood underwent a shift. By 2022, he revealed that he had warmed to the ideas of marriage and children. He attributed this change to his therapy, which helped him deal with past traumas that had inhibited his emotional accessibility and vulnerability. Hamm explained that his work with a therapist, combined with his romance with Osceola that began in 2020, has made his life "even more meaningful" and enabled him to envision a future with marriage, children, and a "new version of happiness, life, wellness."
His wedding to Osceola seems to have solidified his transformed outlook. One attendee shared, "Watching Anna walk down the aisle really moved him. Jon looked at her with such love. It made him proud to be taking this journey with a woman he considers a true partner."
According to a source, Hamm has now wholeheartedly embraced the concept of commitment and looks forward to starting a family with Osceola. Hamm himself hinted at his anticipation for the future in a recent interview, expressing that the future is "exciting. It's exciting because it's all potential, it's all possibility and it's all positive."