After dating for two years, Jon Hamm and Anna Osceola are reportedly engaged, according to People. The pair first got acquainted on the Mad Men set in 2015 after Anna was cast in a minor role as Clementine, the receptionist at Esalen, a spiritual resort in California.

At the time, Jon had been dating Jennifer Westfeldt for 18 years. Throughout their relationship, they regularly expressed their desire to never get married. Representatives for Osceola and Hamm have not yet responded to the report of their engagement.

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Jon Hamm and Anna Osceola’s Relationship Timeline:

After Jon and Jennifer broke up in 2015, he and Osceola were not romantically linked until five years later. Hamm and Osceola, who both avoid social media, were only seen together once in 2017. However, the relationship suspicions started surfacing when they were regularly photographed together in 2020.

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Since then, they have been seen going out for dinners, tennis matches, and beach days. During the early stages of COVID-19, the two were also spotted together purchasing food and supplies in Los Angeles. In September 2021, they also went on a trip together to Italy.

Jon and Anna shared their first red carpet experience as a couple in March 2022 while attending an Oscars after-party. Then, in May, they appeared at the Top Gun: Maverick world premiere and the red carpet premiere of Sarah Silverman’s musical Bedwetter. Together, they also went to the ESPY Awards in July, where they filled the red carpet with PDA.

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Later, in September 2022, they made another on-screen appearance in the comedy-crime movie Confess, Fletch. In the same month, during a visit to Howard Stern’s SiriusXM radio show, Hamm confirmed his commitment to Osceola. When asked if he was in love, Hamm said, “I very much so am.”