After two years of dating, Jon Hamm and Anna Osceola are engaged

The Mad Men co-stars started dating in 2020 and will participate in the 2022 film Confess, Fletch. Jon Hamm and Anna Osceola have gotten married!

The costars of The Confess and Fletch are going to marry after two years of dating, according to PEOPLE. The couple apparently first met on the set of AMC’s Mad Men in 2015, before being spotted together on multiple occasions and romantically linked in 2020.

Hamm’s representative has not responded. Osceola, 34, featured in the series’ penultimate episode as the receptionist at Esalen, a spiritual California retreat visited by Hamm’s character (Don Draper).

Hamm, 51, was in a long-term relationship with Jennifer Westfeldt at the time. After 18 years together, the couple divorced a few months later.

Hamm and Osceola, who both avoid social media, were pictured together once in 2017; relationship speculations began to circulate in 2020 when they were seen out several times.

They’ve been seen going out to eat, playing tennis, and spending time at the beach since then. They also went on a vacation to Italy in September 2021.

They made their red carpet debut at an Oscars afterparty in March 2022, then returning to the red carpet for the Sarah Silverman musical Bedwetter in May, the 2022 ESPY Awards in July, and a screening for their film Confess, Fletch just two months later.

In a SiriusXM interview with Howard Stern in September 2022, Hamm described his connection with Osceola and said that he may see himself marrying someday.

 

“All of this is part of what I’m saying. There is just another location in my life where I feel completely at ease. 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.”

 

“That sounds cheesy and whatever, but it’s true and, for lack of a better word, it’s what I’m aiming for. Apart than that, what more is there?” He went on to say that he is “very much” in love.

In 2022, the two reunited onscreen for the third episode of the Fletch trilogy, Fletch, Confess. In it, Hamm plays semi-retired journalist Irwin M. Fletcher (originally played by Chevy Chase in 1985 and 1989), while Osceala appears in the project as “Larry.”