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Jon Hamm 'pops the question' to 'Mad Men' co-star Anna Osceola after three years of dating

'I'm in now even more meaningful and opened up the possibility of things like being married,' Jon Hamm said in an interview
UPDATED FEB 28, 2023
Jon Hamm and Anna Osceola are engaged (Vivien Killilea/Getty Images)
Jon Hamm and Anna Osceola are engaged (Vivien Killilea/Getty Images)

NEW YORK CITY, NEW YORK: Jon Hamm pops the question to his long-time lover Anna Osceola and the pair are reportedly engaged. Even though Jon Hamm and Anna Osceola are rumored to be dating for three years, sources claim the low-key lovebirds have been together for even longer. The Emmy award winner had previously opened up about his plans to get married to the 'Black Mirror' actress and start a family. 

Hamm said, "(He's) 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," reported Daily Mail. "It sounds hokey and whatever, but it's real and for one of a better word, it's what I'm working for,' he continued. 'What else is there other than that?"

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(L-R) Jon Hamm and Anna Osceola attend the 2022 ESPYs at Dolby Theatre on July 20, 2022 in Hollywood, California.
Jon Hamm and Anna Osceola attend the 2022 ESPYs at Dolby Theatre on July 20, 2022, in Hollywood, California (Leon Bennett/Getty Images)

When did Jon Hamm and Anna Osceola start dating?

Hamm, 51, and Osceola, 34, first met while filming the series finale of 'Mad Men' which premiered in 2015. At the time, Jon was in an 18-year-long relationship with Jennifer Westfeldt but the pair called it quits the same year of Mad Men's premiere. Soon after two years, Hamm and Osceola were first paired in 2017. However, the pair were not romantically linked until early 2020. Since then, Hamm and Osceola have been spotted together running errands during the Covid-19 lockdown and photographed indulging in an intense PDA while on vacation in Italy.

(L-R) Jon Hamm and Anna Osceola attend the Global Premiere of
(L-R) Jon Hamm and Anna Osceola attend the Global Premiere of 'Top Gun: Maverick' on May 04, 2022, in San Diego, California (Amy Sussman/Getty Images for Paramount Pictures)

The 'Top Gun: Maverick' actor and the 'Law & Order True Crime' actress made their red-carpet debut as a couple in March 2022. They were pictured together at the Mercedes-Benz’s Academy Awards viewing party followed by Vanity Fair’s annual afterparty. 'Baby Driver' star also revealed that he is seeking therapy to work on himself after finding out that a lot of his trauma, uncovers from losing his mother due to colon cancer when he was just 10 years old.

'A wound that blocks a lot of that emotional accessibility!'

"It's also been a process of working on myself, my mental health, all the stuff with my therapist," he said. "And unpacking all of that trauma and realizing that when you lose someone that's so important to you, like a mother, so early, that that creates a wound that blocks a lot of that emotional accessibility," according to the source. "That blocks a lot of that availability and vulnerability." Both the lovebirds keep their social lives very private, as the pair is allegedly off social media.

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