Mad Men has not only brought fame and fortune to its star cast but has been creating a buzz in Hollywood for quite some time now given the fact that the lead actors of the series were reportedly engaged. Osceola played the role of Clementine, a receptionist at a spiritual retreat that Jon Hamm's character, Don Draper, attended in Mad Men. Actor Jon Hamm is engaged to his former co-star Anna Osceola. News has not been confirmed by the stars yet, but People Magzine has reportedly given an affirmation.
Firstly, Hamm and Osceola met on the sets of Mad Men in 2015 when he was in a long-term relationship with Jennifer Westfeldt. Both stayed in touch after their show got wrapped up. They were seen together buying coffee in 2017. Until May 2020, there was no news but later they were seen hanging out on the beach, and rumours about their relationship started surfacing online.
After that, the duo was seen at several events and parties like the Vanity Fair Oscars party earlier this year. In a recent interview, Hamm termed their relationship "comfortable" and dropped hints about his future plans to get married and have kids.
Hamm was in a long-term relationship with Westfeldt before starting dating Osceola, and then they split up harmoniously. Per the reports, the couple has separated due to Jon's substance issues and frequent partying.