Jon Hamm and Anna Osceola are gearing up for a new chapter in their lives as they prepare to welcome their first child together in September 2024. The couple, who first crossed paths while working on the critically-acclaimed series *Mad Men*, have been married since June 2023.
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Their connection blossomed during the show’s production, where Hamm portrayed the iconic advertising executive Don Draper from 2007 until 2015. Osceola made a brief appearance in the series finale, portraying a receptionist at Esalen, a retreat Don visits. This small role marked the beginning of their shared journey in the entertainment industry.
Hamm and Osceola’s romantic relationship reportedly began in earnest after they finished filming *Mad Men*; the couple made their public debut together in March 2022 at an Oscars afterparty, marking a significant milestone in their relationship after nearly two years of dating. Their subsequent appearances at various events, including the ESPY Awards and the 2023 LACMA Art + Film Gala, showcased their growing partnership.
In February 2023, news broke that the pair had become engaged, a development that Hamm confirmed shortly thereafter. Shortly after, the public got its first glimpse of Osceola’s stunning engagement ring, featuring an emerald-cut diamond set on a simple gold band. In an interview, Hamm admitted to feeling “terrified” at the prospect of proposing, a sentiment shaped by his own childhood experiences with divorce. He expressed that the nervousness felt right, implying that the weight of such a moment underscored its significance.
The couple exchanged vows on June 24, 2023, in a picturesque ceremony held at Anderson Canyon in Big Sur, California. Their wedding guest list included notable names such as Billy Crudup, Paul Rudd, and Tina Fey. Leading up to the ceremony, Hamm spoke about the excitement of marriage, describing it as an endeavour that offers “stability and comfort.” He noted that the bond between partners should evolve beyond casual labels, highlighting the deeper connection that marriage represents.
Both Hamm and Osceola have continued to collaborate professionally since their time on *Mad Men*. They appeared together in the 2022 film *Confess, Fletch*, in which Hamm played the lead role as Irwin M. Fletcher, while Osceola took on the character of Larry. Looking ahead, they will reunite once more in the Apple TV series *Your Friends & Neighbors*, where Osceola has been cast for a role in the second season.
In August 2026, it was confirmed that the couple is expecting their first child. The news comes shortly after Hamm expressed his views on fatherhood in an interview with *The Hollywood Reporter*, noting his age as a factor in his approaching parenthood. He acknowledged, “It’s not lost on me that I’m 53. I will be the old dad, but so it goes.” Hamm seems optimistic about the prospect, suggesting that being an older father might bring unique benefits.
As Jon Hamm and Anna Osceola look forward to becoming parents, their growing family represents not just a personal milestone, but also an exciting new phase for a couple who have supported one another throughout their careers. Their shared journey showcases the harmony between marriage and professional collaboration in the demanding world of acting. With the impending arrival of their child, fans of both actors eagerly await the next chapter in their lives.