Jon Hamm and Anna Osceola's Relationship Timeline

Not only did Jon Hamm win an Emmy for his role as Don Draper on Mad Men, but the show introduced him to his wife, Anna Osceola.

The actors met while filming the series finale of the AMC drama in 2015, as Osceola played Clementine, a receptionist at the retreat Hamm’s character attended. Though briefly linked in 2017, Us Weekly confirmed the couple’s romance in June 2020. After nearly three years of dating, Hamm took things to the next level by popping the question to Osceola.

Though neither are on social media, they have shared several fun moments over the years, from red carpet appearances to European vacations to sharing the screen again and more. Staying out of the spotlight seemed to do the trick, as the Top Gun: Maverick star admitted that he could “for sure” see himself settling down with Osceola on The Howard Stern Show in September 2022.

Hamm and Osceola said “I do” in June 2023 in an outdoor ceremony at Anderson Canyon in Big Sur, California.

Before Osceola, Hamm was in an 18-year-long relationship with actress Jennifer Westfeldt. Together since 1997, the pair called it quits in September 2015. A source told Us at the time that although the two “definitely tried” to make things work, there was “always a rift” between them, noting, “He wanted kids and she didn’t.”

Hamm opened up about the breakup in a June 2017 interview with InStyle. “It’s fine,” he said, adding, “It’s hard. It’s hard to be single after being together for a long time. It’s really hard. It sucks.”

Scroll below to relive Hamm and Osceola’s sweetest relationship moments: