Jon Hamm reveals he might marry girlfriend Anna Osceola for 'new version of happiness'

Hamm said that his relationship with Osceola had been crucial to his 'process of working on [himself]' and 'unpacking' the trauma of losing his mother

Jon Hamm reveals he might marry girlfriend Anna Osceola for 'new version of happiness'
Jon Hamm speaks candidly about the prospect of getting married to Anna Osceola, his girlfriend of two years. (Frazer Harrison/Getty Images)
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NEW YORK CITY, NEW YORK: The year 2020 saw the beginning of Jon Hamm's relationship with Anna Osceola, and things seem to be getting better for him romantically. Hamm, 51, stated during an interview with Howard Stern that he is "very much" in love with his girlfriend Osceola, 34, and hinted that they would be married soon.

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On Monday, September 19, the 'Mad Men' actor claimed during an interview with Stern on his SiriusXM show that Osceola has been supporting him as he works on himself, which has made their relationship "even more meaningful and opened up the possibility of things like being married, having kids, you know, defining a new version of happiness, life, and wellness. All that stuff that sounds hokey and whatever but it's real and, for want of a better word, it's what I'm working for. What else is there other than that."

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The 'Million Dollar Arm' actor claimed that his relationship with Osceola had been crucial to his "process of working on [himself]" and "unpacking" the trauma of losing his mother at the age of 10. Losing his mother, according to Hamm, has prevented him from being "emotional accessibility, availability and vulnerability."

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When Stern questioned whether he was in love with Osceola, Hamm stated, "I very much so am," and while describing his relationship, he said, "It's good and comfortable and it's a feeling about taking care of someone else and being taken care of," adding that he "could for sure" picture himself marrying her.

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The couple, who starred together in the movie 'Confess, Fletch', had successfully kept their romance private, however in September 2021, they were photographed engaging in intense PDA while on vacation in Italy. When they appeared for pictures at the Mercedes-Benz Academy Awards viewing party and Vanity Fair's annual afterparty in March 2022, Hamm and Osceola made their red carpet debut as a couple.

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Jon Hamm and Anna Osceola attend
Jon Hamm and Anna Osceola attend "Confess, Fletch" screening at The West Hollywood EDITION on September 07, 2022 in West Hollywood, California. (Photo by Robin L Marshall/Getty Images)

Osceola first met with Hamm on the set of 'Mad Men' in 2014, where she made her on-screen debut as Clementine in the season finale. At the time, Hamm was committed to screenwriter and actress Jennifer Westfeldt. The 'Fargo' star had been together with Westfeldt since 1997, but they eventually called it quits in 2015.

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After nearly 18 years of dating, the former couple felt it was too difficult to maintain their partnership together and ended their relationship. They announced their split in a joint statement, claiming to "continue to support each other in every way moving forward." Rumors of Hamm dating Osceola eventually started to circulate, but they remained secretive about their relationship up until the start of 2020. Since that time, their relationship seemed to be going strong.

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Mercedes-Benz ambassador Jon Hamm and Anna Osceola arrive at the 2022 Mercedes-Benz Academy Awards Viewing Party at the Four Seasons Hotel Los Angeles in Beverly Hills on March 27, 2022 in Los Angeles, California.
Jon Hamm and Anna Osceola arrive at the 2022 Mercedes-Benz Academy Awards Viewing Party at the Four Seasons Hotel Los Angeles in Beverly Hills on March 27, 2022 in Los Angeles, California. (Photo by Vivien Killilea/Getty Images for Mercedes-Benz)

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