There's no denying that Jon Hamm has his starring role as Don Draper in Mad Men, a period drama about the advertising industry in the 1960s, to thank for his career success; the hit AMC series earned him an Emmy, two Golden Globes, and a Screen Actors Guild award and made Hamm a household name. What most people don't know is that his time on Mad Men also helped him with his romantic life. Hamm met Anna Osceola, with girlfriend of nearly two years, on set in 2015, and now the former co-stars are ready to take their relationship to the next level. According to People, Hamm and Osceola are officially engaged.
Osceola appeared in the final episode of the hit series, playing the receptionist at Esalen, a spiritual retreat that Don Draper attended. While they were filming, Hamm was in a long-term partnership with Jennifer Westfeldt, but he ended it in 2015 after 18 years together. In June of 2017, the Top Gun: Maverick actor opened up about his decision to part ways. “It’s hard,” he admitted. “It’s hard to be single after being together for a long time. It’s really hard. It sucks.”
After breaking up with Westfeldt, Hamm was spotted with Jenny Slate in June of 2017, but sources told People their relationship was strictly friendly. In September of 2019, the actor attended the Broadway premiere of Derren Brown: Secret with Saturday Night Live producer Lindsay Shookus. Then, in 2020, Hamm and Osceola sparked dating rumors. Throughout their two years together, the couple has been seen enjoying dinner dates, playing tennis, spending time at the beach, and taking a trip to Italy, but for the most part, they keep their relationship pretty private.
In March of 2022, the couple made their first red carpet appearance at an Oscars after-party. Two months later, they attended another event together for the Sarah Silverman musical, Bedwetter, and two months after that, they graced the red carpet at the 2022 ESPY Awards. The two were also co-stars in the comedy and crime movie Confess, Fletch, so to promote their 2022 film, they showed up to the screening together in September of 2022.
Even though Hamm and Osceola don’t disclose many of the details about their relationship, the soon-to-be groom did tell Howard Stern on his SiriuisXM show in September of 2022 that he can see himself getting married to Osceola and that he’s “very much so” in love. “This is all part of what I’m saying,” he begins, referring to his experience working on his mental health and talking to a therapist. “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 also explained that dating Osceola has opened up the possibility of marriage, children, and feeling a new level of happiness. “It sounds hokey and whatever, but it's real and for one of a better word, it's what I'm working for,” he says. “What else is there other than that?”