Jon Hamm and Anna Osceola Are Married—and Their Wedding Included a "Mad Men" Nod!

Not only did Mad Men grant Jon Hamm numerous awards for starring as main character Don Draper on the hit period drama, but the stint also introduced him to Anna Osceola, who he can now call his wife. Eight years after the couple met on set, the actors became husband and wife. On June 24, 2023, TMZ first announced the news that the co-stars tied the knot, and People confirmed their marriage the following day. 

According to TMZ, the pair got married at Anderson Canyon in Big Sur, California, which happens to be the same spot where the duo first met during the Mad Men finale. Their wedding was a star-studded affair: Celebrities, such as Tina Fey, Paul Rudd, and Billy Crudup, witnessed their vow exchange, the outlet reports. The publication also notes that the couple’s processional song was “You Only Live Twice” by Nancy Sinatra, the theme song to the 1967 James Bond film, You Only Live Twice. Based on the photos obtained by TMZ, Osceola donned a strapless ball gown with a dramatic slit and a plunging neckline, while Hamm looked dapper in a black tuxedo and bow tie.

In 2015, Hamm was wrapping up the final episode of Mad Men, when he crossed paths with his now wife. While Hamm played the main character across all seven seasons of the popular AMC series, Osceola just appeared in the finale. In the episode, Osceola played the receptionist at Esalen, a spiritual retreat that Hamm’s character attended. At the time, Hamm was in a long-term relationship with Jennifer Westfeldt, but that same year, he ended their union after 18 years together. In June 2017, the actor opened up about his decision to part ways. “It’s hard,” he admitted. “It’s hard to be single after being together for a long time. It’s really hard. It sucks.”

After ending things with Westfeldt, Hamm wasn’t romantically linked with Osceola until 2020. Although the couple was spotted enjoying dinner dates, playing tennis, and spending time on the beach, they kept their relationship private. In fact, they didn’t make their red carpet debut until March 2022 at the Vanity Fair Oscars Party. That same year, Hamm told host Howard Stern on The Howard Stern Show that he was “very much” in love—without explicitly saying Osceola’s name. "This is another place in my life that I feel very settled and comfortable,” he said. “I’m in a relationship right now, and it’s comfortable.” 

He also explained that dating Osceola has given him newfound happiness and the possibility of getting married and starting a family together. “It sounds hokey and whatever, but it's real and for one of a better word, it's what I'm working for,” he noted. “What else is there other than that?” During his cover story interview with Parade in 2010, Hamm admitted that he never intended to get married, mainly because his parents’ marriage didn’t last. But in February 2023, People confirmed in February 2023 that Hamm popped the question to Osceola.