Jon Hamm and Anna Osceola Are Reportedly Engaged

After two years of dating, Jon Hamm and Anna Osceola are ready to spend the rest of their lives together.

The Confess, Fletch co-stars are engaged after they first started dating in 2020, per People. The two actors technically met for the first time back in 2015 on the set of Mad Men in which Hamm played the lead role of Don Draper and Osceola appeared in the final episode of the series as Clementine, a receptionist at a spiritual retreat Draper checks into. However, it wasn’t until five years later that things became romantic between the two as during their first meeting Hamm was still in a relationship with his longtime girlfriend Jennifer Westfeldt. He and Westfeldt broke up just a few months after the end of the show after 18 years together. In 2020, speculation began that Hamm and Osceola were dating after they were spotted out together on several different occasions throughout the pandemic. And, by September 2021, their relationship was all but confirmed when the couple took a vacation to Italy together. In March 2022, they made things red carpet official at an Oscars afterparty, followed by another step-and-repeat appearance together in May at the opening of Sarah Silverman‘s Bedwetter.

While Hamm and Osceola have remained very private about their relationship, The Town actor did reveal that because of Osceola he was starting to think about marriage and children for the first time. “This is all part of what I’m saying. This is another place in my life that I feel very settled and comfortable. I’m in a relationship right now and it’s comfortable,” he said during a September 2022 interview on Howard Stern‘s SiriusXM show. “It’s a feeling of taking care of someone else and being taken care of.”

He went on to explain that the success of their relationship is the result of “a process of working on myself, my mental health, all the stuff with my therapist and unpacking all of that trauma and realizing that when you lose someone 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 lost his mother when he was 10 years old to colon cancer, and his father died ten years after that. He continued, “It’s only been in the last couple of years, me kind of sitting down and really thinking about all that stuff, that’s made the relationship that I’m in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness.” Hamm concluded, “It sounds hokey and whatever, but it’s real and it’s—for want of a better word—it’s what I’m working for. What else is there other than that?” He also confirmed that he is “very much” in love.