Jon Hamm Got Engaged To His Girlfriend Of Two Years, Anna Osceola

February 28, 2023 / Posted by:

Back in 2022 when John Hamm was out promoting his film, Confess, Fletch, there were two talking points he found pertinent: assuring everyone that despite his oft-visible Hammaconda’s years-long run leading everyone to believe he was against underwear, he’s never gone without them; and that he was very in love with his girlfriend at the time, Anna Osceola. While it’s still hard to believe that he’s never gone commando, it seems like he was telling the truth about his love for Anna; because People confirmed they’re engaged, though neither of the betrothed shared more details.

Jon and Anna first met in 2015 when she had a small role in the series finale of Mad Men, but Jon was still in a long-ass relationship with Jennifer Westfeldt then. A while after that relationship ended, Jon and Anna got together and have now been an item for at least two years. They also appeared in Confess together.

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.

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. 

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.

Hamm’s rep has not commented.

Jon doted on his and Anna’s relationship and toyed with the idea of marriage a few months ago; so move over, boxer briefs, Anna’s here to hold Jon tight from now on. Hopefully, she does a better job than these.

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.

Congratulations to Jon and Anna! May this union be filled with zero bull dicks and only “fabulous food, a little fabulous conversation, fabulous foot massages, and plenty of evenings filled with TOTAL FABULOSITY.” 

Pic: Xavier Collin/ABACA/ Images

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