Secret Romance Revealed! Jon Hamm and Anna Osceola Tied the Knot in an Epic 'Mad Men'-Inspired Wedding

Jon Hamm and Anna Osceola. AFF-USA/Shutterstock

Jon Hamm and his longtime girlfriend, Anna Osceola, exchanged vows in a picturesque outdoor ceremony on Saturday, June 24. The enchanting Anderson Canyon in Big Sur, California, where the iconic TV show Mad Men was filmed, served as the perfect backdrop for their wedding. Coincidentally, Hamm's character, Don Draper, found inspiration for the legendary 1970 “Hilltop” Coca-Cola ad at this very location, while Osceola's character, Clementine, worked as a receptionist there.

Their Mad Men co-star, John Slattery, was in attendance to witness the marriage of Osceola, 35, and Hamm, 52. Other notable celebrities present at the star-studded event included Billy Crudup, Paul Rudd, Tina Fey, Brooke Shields, and Larry David.

As the audience looked on, Osceola gracefully made her way down the aisle wearing a beautiful strapless white gown with a neckline that revealed a hint of allure and a back that was elegantly low. The dress, accentuated by a high slit, allowed her legs to be showcased as she walked. Completing her bridal ensemble, the Massachusetts native adorned herself with dainty gold bracelets and a delicate necklace. Wanting a natural and romantic look, Osceola styled her hair in loose curls. And finally, she held a breathtaking bouquet of soft pink peonies.

The bride and groom briefly dated in 2017, but their relationship became official in June 2020. They made their first public appearance as a couple at an Oscars viewing party in March 2022 and also worked together in the film Confess, Fletch in September 2022.

During the promotion of the comedy, Hamm hinted at the seriousness of their romance. In a September 2022 interview on The Howard Stern Show, the Good Omens actor described their relationship as comfortable and expressed a sense of mutual care. He openly discussed the possibility of marrying Osceola, stating that he could definitely see it happening.

Jon Hamm and Anna Osceola. Adela Loconte/Shutterstock

The Emmy award-winning actor explained that undergoing therapy to process the difficulties of his childhood has had a positive impact on his current relationship. He revealed to Howard Stern that this experience has deepened the meaning of his relationship and allowed him to consider possibilities such as marriage and starting a family. This process has allowed him to redefine happiness, life, and well-being in a genuine way. Hamm acknowledged that these ideas may sound cliché, but they are his driving force. He questioned what else could be more important than these aspects of life.

Several months later, it was confirmed that the couple had gotten engaged. An exclusive source told Us magazine in February that the engagement had taken place earlier, and the couple was still riding the wave of happiness. They have a great time together and already feel like they are married.

Prior to his relationship with Osceola, Hamm was involved in a romantic partnership with actress Jennifer Westfeldt for a span of 18 years. Unfortunately, their relationship came to an end in September 2015. According to an insider, despite their efforts to hold on, a perpetual rift existed between them. Their differing desires regarding having children seemed to be a major factor contributing to the rift.