Anna Osceola and Jon Hamm get 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 apparently initially met in 2015 on the set of the AMC series Mad Men.
Anna Osceola and Jon Hamm are now engaged
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 at the time. 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 been seen leaving 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 that he may see himself getting married in the future when talking about his relationship with Osceola.
“All of this is included in what I’m saying. Another area of my life where I feel content and at ease is this one. I’m in a relationship right now, and it’s comfortable,” he said, later adding that he had the opportunity to sit down and begin “really thinking about all that stuff, which has made the relationship that I’m in right now even more meaningful and opened up the possibility of things like being married, having children, and defining a new version of happiness, life, and wellness.”
“While it may seem corny and other things, it’s real and, for lack of a better phrase, that’s what I’m striving for. Apart than that, what more is there?” Before stating that he is “very much so” in love, he added.
In 2022, they collaborated once more for Fletch, Admit, the third episode of the Fletch series. In it, Osceala makes an appearance as “Larry,” while Hamm plays the semi-retired journalist Irwin M. Fletcher (previously portrayed by Chevy Chase in 1985 and 1989).
