Is Jon Hamm And Anna Osceola Are Engaged?

After dating for two years, the Admit, Fletch co-stars are getting married, PEOPLE has confirmed. Before being repeatedly seen together and romantically linked in 2020, the duo initially met in 2015 on the set of the AMC series Mad Men.

Osceola, 34, made a brief appearance in the series’ concluding episode as the receptionist at Esalen, a spiritual retreat in California that Don Draper, played by actor Jon Hamm, went. Hamm, 51, had been seeing Jennifer Westfeldt for a while. After 18 years together, the couple separated a few months later.

Hamm and Osceola, who both avoid social media, were only seen together once in 2017; relationship suspicions began to spread when they were repeatedly spotted together in 2020. Since then, they have left the house for meals, tennis matches, and beach days. In September 2021, they also went on a trip together to Italy.

They first appeared on the red carpet in March 2022 at an Oscars afterparty. They then made another appearance on the red carpet in May for the Sarah Silverman comedy Bedwetter, attended the 2022 ESPY Awards in July, and attended a screening for their film Confess, Fletch barely two months later.

In a SiriusXM interview with Howard Stern in September 2022, Hamm claimed he might see himself getting married when discussing his relationship with Osceola.

Is Jon Hamm And Anna Osceola Are Engaged?

“This is all part of what I’m saying. This is another place where 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.

In 2022, they collaborated once more for Fletch, Admit, the third episode of the Fletch series. In it, Osceola appears as “Larry,” while Hamm plays the semi-retired journalist Irwin M. Fletcher (previously portrayed by Chevy Chase in 1985 and 1989).

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