Who Is Jon Hamm’s Girlfriend? All About Anna Osceola

Jon Hamm keeps his personal life private, including his relationships.


Hamm has been dating actress Anna Osceola since 2020 after the couple reportedly met on the set of Mad Men in 2015.


Before dating Osceola, Hamm was in a long-term relationship with Jennifer Westfeldt. However, the couple split in 2015 after 18 years together.


During a June 2017 interview with InStyle, Hamm took a rare moment to open up about his private life, including his relationship status. He got candid about being single, telling the outlet, “It’s hard. It’s hard to be single after being together for a long time. It’s really hard. It sucks.”


Following his split with Westfeldt, Hamm was spotted with Jenny Slate in June 2017, with sources telling PEOPLE at the time that the two were “friendly.” In September 2019, Hamm stepped out with former Saturday night Live producer Lindsay Shookus at the Broadway premiere of Derren Brown: Secret.


While Hamm and Osceola were photographed together in 2017, they didn’t spark romance rumors until years later in 2020. Since then, they’ve been spotted a handful of times throughout the course of their two-year relationship and have made a few red carpet appearances, though they keep much of the details of their romance under wraps.


During an interview with Howard Stern on his SiriusXM show on Sept. 19, 2022, in rare fashion, Hamm discussed his relationship with Osceola. When asked by Stern if he would ever be able to be married, Hamm replied that he could see himself making that milestone someday.


“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, explaining that he’s been working on himself and his mental health with a therapist.


Hamm said that over the course of the last couple of years, 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 children, defining a new version of happiness, life, wellness.”


He continued, “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.


So, who is Jon Hamm’s other half? Keep reading for everything to know about Anna Osceola and her relationship with the actor.



She was born in Massachusetts

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Osceola was born on April 8, 1988, in Cambridge, Massachusetts, where she grew up before relocating to California to pursue acting.



She is an actress

Osceola made her acting debut in 2007 when she appeared in the television movie Not Another High School Show as the character Charlie. Throughout her career, she made appearances on a host of popular shows, including a three-episode arc on Greekas well as roles on Rizzoli & Isles, NCIS, Law & Order: Special Victims Unit and Law & Order True Crime.



They met on the set of Mad Men

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Hamm and Osceola reportedly first crossed paths on the set of Man Men, after she had a small role in the final episode of the show. Osceola played the receptionist at Esalen, a spiritual California retreat that Hamm’s character, Don Draper, attended.



They’ve been dating since 2020

Hamm and Osceola were first linked romantically in 2020, when they were spotted together on several occasions. Since then, the pair have been photographed stepping out for meals, playing tennis and enjoying a day at the beach. They even took a vacation to Italy together in September 2021, where they were seen relaxing on the water.



They appear together in Hamm’s new movie Confess, Fletch

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Hamm and Osceola appeared on the screen together again for the third installment of the fletch series. Hamm tackles the role of the semi-retired journalist Irwin M. Fletcher, originally played by Chevy Chase in the 1985 movie fletch and the subsequent 1989 movie Fletch Lives. In the 2022 film, Hamm’s character becomes involved in an investigation of an art heist. Osceala also appears in the project, playing the role of “Larry.”



They both stay off social media

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Both Hamm and Osceola live their lives off of social media. The couple is decidedly low-key and keeps their personal lives, including their relationships, private and away from the public eye. Hamm has opened up about his decision to set boundaries in the industry and retain his own sense of self, telling InStyle in 2017, “The point of life is not to put dog ears on yourself and post it online for everyone to see.”


“It’s fun, it’s adorable, but it’s the visual equivalent of masturbating—there’s no point other than immediate gratification,” he added.



They made their red carpet debut in March 2022

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Hamm and Osceola took a big step in their relationship in March 2022 when they made their red carpet debut at an Oscars afterparty. The couple attended the annual viewing party hosted by Mercedes-Benz, followed by an appearance at the Vanity Fair Oscars afterparty.


Since then, they’ve made several other appearances together, including on the red carpet for the Sarah Silverman musical. Bedwetter in New York City in May, at the 2022 ESPY Awards in July and at a screening for Confess, Fletch in September.

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