Jon Hamm and Anna Osceola Are Engaged After Two Years of Dating
Chelsea Lauren/Shutterstock Jon Hamm and Anna Osceola
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.
Hamm's rep has not commented.
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Timothy Norris/FilmMagic Jon Hamm and Anna Osceola
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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In March 2022, they made their red carpet debut at an Oscars afterparty, before stepping out yet again at the red carpet for the Sarah Silverman musical Bedwetter in May, appearing at the 2022 ESPY Awards in July and showing up to a screening for their movie Confess, Fletch just two months later.
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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 being married some day.
"This is all part of what I'm saying. 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 said, later adding that he's been able to sit down to start "really thinking about all that stuff, that's made the relationship that I'm in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness."
"It sounds hokey and whatever, but it's real and for one of a better word, it's what I'm working for. What else is there other than that?" he added before confirming that he is "very much so" in love.
The two joined forces onscreen again in 2022, for the third installment of the Fletch series, Fletch, Confess. In it, Hamm takes on the role of semi-retired journalist Irwin M. Fletcher (originally played by Chevy Chase in 1985 and 1989), while Osceala appears in the project, playing the role of "Larry."
