Jon Hamm and Anna Osceola are engaged after two years of dating

Jon Hamm and Anna Osceola are engaged after two years of dating The Mad Men costar began dating in 2020 and appeared together

Feb 28, 2023 - 09:20
Feb 28, 2023 - 09:20
 0
Jon Hamm and Anna Osceola are engaged after two years of dating
Jon Hamm and Anna Osceola are engaged after two years of dating

Jon Hamm and Anna Osceola are engaged after two years of dating
The Mad Men costar began dating in 2020 and appeared together in the 2022 film Confess, Fletch

   Jon Hamm and Anna Osceola are engaged!

Confess, Fletch Coster is getting married after two years of dating, PEOPLE confirms. The pair reportedly first met on the set of the AMC series Mad Men in 2015, before being spotted together on several occasions and being romantically linked in 2020.

Jon Hamm and Anna Osceola are engaged after two years of dating

A representative for Hamm did not comment.

   Osceola, 34, appeared in the series finale, where she had a small role as the receptionist at Esalen, a spiritual California retreat attended by Hamm's character (Don Draper). At the time, Hamm, 51, was in a long-term relationship with Jennifer Westfeldt. The couple broke up a few months later after 18 years together.

Hamm and Osceola, who both keep social media off, were photographed together once in 2017; Rumors of romance started in 2020 when they were spotted multiple times. Since then, they have been spotted going out for meals, playing tennis and enjoying a day at the beach. They vacationed together in Italy in September 2021.

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In March 2022, they made their red carpet debut at an Oscars afterparty, before stepping out on the red carpet again for the Sarah Silverman musical Bedwetter in May, appearing at the 2022 ESPY Awards in July, and attending a screening of their movie. Admittedly, Fletch is only two months later.

   Hamm discussed his relationship with Osceola in a September 2022 interview with Howard Stern on his SiriusXM show, when he revealed that he could see himself getting married one day.

"That's all part of what I'm saying. It's another place in my life where I feel very settled and comfortable. I'm in a relationship right now and it's comfortable," she said, later adding that she's been able to start "really." Think about all these things, it made the relationship I'm in so much more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, well-being."

"It sounds hokey and whatever, but it's real and for a better word, I'm working on it. What else is there?" She added before confirming that she was "very much" in love.

The two reunited onscreen in 2022 for Fletch, Confess, the third installment in the Fletch series. In it, Hamm is semi-retired journalist Irwin M. landed the role of Fletcher (originally played by Chevy Chase in 1985 and 1989), while Ossala plays "Larry" in the project.

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