TV Jon Hamm is engaged to Mad Men costar Anna Osceola The two have been dating for two years. By Jessica Wang Jessica Wang Jessica is a staff writer at Entertainment Weekly, where she covers TV, movies, and pop culture. Her work has appeared in Bustle, NYLON, Cosmopolitan, InStyle, and more. She lives in California with her dog. EW's editorial guidelines Published on February 27, 2023 06:42PM EST Jon Hamm and Anna Osceola are engaged after two years of dating, PEOPLE reports. The two are believed to have met on set of the hit AMC period drama Mad Men, during the seventh and final season in 2015. Osceola portrayed Clementine, the receptionist at the spiritual retreat that Hamm's lead ad executive character Don Draper attended, in the series finale, though Hamm and Osceola were not romantically linked until 2020. Osceola also recently appeared alongside Hamm in the 2022 crime comedy Confess, Fletch. The pair made their red carpet debut last year at an Oscars afterparty. Jon Hamm and Anna Osceola. Tommaso Boddi/Getty Last September, Hamm appeared on Howard Stern's SiriusXM show and said he was at a "comfortable" stage in his life where he could envision himself getting married. "I'm in a relationship right now and it's comfortable," he said. "It's a feeling of taking care of someone else and being taken care of." "It's also been a process of working on myself, my mental health, all the stuff with my therapist," Hamm said. "And unpacking all of that trauma and realizing that when you lose someone that's so important to you, like a mother (Hamm's mother died when he was 10) , so early, that that creates a wound that blocks a lot of that emotional accessibility, that blocks a lot of that availability and vulnerability." He added, "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. It sounds hokey and whatever, but it's real and it's what I'm working for." Reps for Hamm and Osceola didn't immediately respond to EW's request for comment. Related content: Jon Hamm revives everyone's favorite smartass investigative reporter in Confess, Fletch trailer How Jon Hamm and Greg Mottola broke the Fletch curse: By saying 'f--- it' Jon Hamm is returning for Good Omens season 2 — and he's bringing more angels