Jon Hamm and Anna Osceola’s Relationship Timeline: From ‘Mad Men’ to Their Engagement and More

Mad for each other. Not only did Jon Hamm win an Emmy for his role as Don Draper on Mad Men, but the show introduced him to the love of his life, 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. “The engagement happened a while back, but they are still on cloud nine,” a source revealed to Us in February 2023. “They have so much fun together and already feel married.” 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. Stating that their relationship is “comfortable,” the Unbreakable Kimmy Schmidt alum explained to host Howard Stern, “It’s a feeling of taking care of someone else and being taken care of. And it’s also been a process of working on myself, my mental health, all the stuff with my therapist, and unpacking all of that trauma and realizing that, you know, when you lose somebody, like, that’s so important to you — like a mother — so early, that that creates a wound that blocks a lot of that emotional accessibility, that blocks a lot of that availability and vulnerability.” Hamm told ABC News in October 2016 that he lost his mother, Deborah Hamm, to colon cancer when he was 10 years old. He continued: “It’s only been in the last couple of years of me kind of sitting down and really thinking about all that stuff that’s made the relationship that I’m in now, is even more meaningful, and opened up the possibility of being married, having kids, defining a new version of happiness, life, wellness. All that stuff, it sounds hokey and whatever, but it’s real.” 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.” The Good Omens actor 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.”Sign up for Us Weekly's free, daily newsletter and never miss breaking news or exclusive stories about your favorite celebrities, TV shows and more! Scroll below to relive Hamm and Osceola’s sweetest relationship moments: