Jon Hamm and Anna Osceola's Complete Relationship Timeline

Jon Hamm and Anna Osceola have been going strong since tying the knot in June 2023, and their love story began years earlier on the set of Mad Men. The two first met in 2015 when Osceola made a brief appearance in the series finale as Clementine, a receptionist at the retreat Hamm’s character, Don Draper, attended. Their connection would later evolve into a romance that led to their red carpet debut, engagement, and eventual wedding.

Both Hamm and Osceola have carved out careers as actors in the entertainment industry, both supporting each other's endeavors over the years. Hamm skyrocketed to fame as Don Draper on Mad Men, earning critical acclaim and a devoted fanbase. He has since continued to take on a wide range of roles in film and television, with his upcoming Apple TV+ series, Your Friends and Neighbors, premiering on April 11. 

Meanwhile, Osceola, also an actor, has appeared in projects like Greek and Law & Order: Special Victims Unit. The couple reunited on screen, too, both starring in a 2022 film, Confess, Fletch. Though she keeps a lower profile than Hamm, she has become a familiar face at Hollywood events alongside her husband.

From their first on-screen meeting to their real-life romance, Hamm and his wife's relationship has unfolded in a way that feels both fateful and enduring. Below, take a closer look at the pair's full dating timeline, from their early beginnings to their life as a married couple.

2015: The Initial Meeting

Hamm and Osceola first crossed paths while filming the series finale of Mad Men. Osceola played Clementine, a receptionist at the retreat Hamm’s character attended. At the time, there was no indication of a romance brewing, but little did they know they'd end up married just years later. 

2017: Romance Rumors

Hamm has always been quieter in the public eye, so when he was spotted with Osceola in the evening, what could have been after a dinner date, the two sparked romance rumors online. However, the buzz quickly died down as there was no other confirmation of a relationship. 

2020: Hamm and Osceola Officially Dating

It wasn't until 2020 that the pair was officially linked romantically, with sources confirming the couple's relationship after a few quiet appearances here and there. However, with the pandemic, we weren't seeing much of anyone out in public. 

March 2022: The Relationship Debut

The couple finally made their relationship public in March 2022 when Hamm brought Osceola as his plus one to the Vanity Fair Oscars Party. The couple posed on the carpet together, marking their first of what would be many red carpet appearances. 

February 2023: Hamm Proposed to Osceola

Since both Hamm and Osceola are relatively private people, there's not much information on the details, but it was announced that Hamm proposed to Osceola in February of 2023, after three years of being publicly linked to one another. This was a first for both of them, as Hamm has never been married, let alone engaged before. (He was in a long-term partnership with Jennifer Westfeldt, from 1977 to 2015, before Osceola.)

June 2024: The Wedding

The couple tied the knot at Anderson Canyon in Big Sur, California—the very location where the Mad Men finale was filmed. It was perfectly romantic and meaningful to Hamm and Osceola.

2024-2025: Red Carpet Appearances

Since their wedding, the couple has stayed off social media but continues to appear together at red carpet events, openly showing their affection. Most recently, they were seen sharing sweet moments at Saturday Night Live's 50th Anniversary Special and the 2025 Vanity Fair Oscars Party.