Jon Hamm and Anna Osceola are engaged!

The Confess, Fletch costars are set to wed after two years of dating, PEOPLE confirms. The pair first reportedly met on the set of the AMC series Mad Men in 2015, before being spotted together on several occasions and romantically linked in 2020.Osceola, 34, appeared in the series' final episode, where she had a small role playing the receptionist at Esalen, a spiritual California retreat that Hamm's character (Don Draper) attended. At the time, Hamm, 51, was in a long-term relationship with Jennifer Westfeldt. The couple split months later after 18 years together.

Hamm and Osceola, who both keep off social media, were photographed together once in 2017; romance rumors took off in 2020 when they were seen out multiple times. Since then, they've been spotted stepping out for meals, playing tennis and enjoying a day at the beach. They also took a vacation to Italy together in September 2021.

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