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

Jon Hamm does not talk about his dating history or other aspects of his private life. After apparently meeting in 2015 on the set of Mad Men, Hamm has been seeing actress Anna Osceola since 2020.

Hamm had a long-term romance with Jennifer Westfe

ldt before he started dating Osceola. Despite being together for 18 years, the pair finally broke up in 2015.

During an interview with InStyle published in June 2017, Hamm discussed his personal life for the first time in years, including his dating status. The actor opened out to the media about his single status, saying, “It’s not easy. After a long time together, it can be difficult to be on your own. To put it simply, it’s not easy. Basically, it’s terrible.”

After his breakup with Westfeldt in June 2017, Hamm was reportedly seen with Jenny Slate, with insiders telling PEOPLE that they were “friendly.” Hamm attended the Broadway opening of Derren Brown: Secret in September 2019 with former SNL producer Lindsay Shookus.

Photographs of Hamm and Osceola together in 2017 did not lead to any speculation about a romantic relationship between them until 2020. They’ve been together for two years and have made a few public appearances together during that time, including on the red carpet, but they’ve kept the specifics of their relationship under wraps.

Hamm was candid about his connection with Osceola during a rare appearance on Howard Stern’s SiriusXM broadcast on September 19, 2022. Hamm said he could eventually get married when Stern questioned if he thought he would be able to do so.

“All of this is relevant to what I’m trying to express. Like most of my other life circumstances, this one has become rather familiar and comfortable to me. I’m currently in a stable relationship, “He elaborated by telling us he’s been seeing a therapist to improve his emotional well-being.

Hamm stated that “truly thinking about all that stuff” has allowed him to “make the relationship that I’m in now even more important and opened up the potential of things like being married, having kids, defining a new version of happiness, life, wellness” during the past few years.

He elaborated, “It’s corny, but in a way that describes my goal in life; it’s the truth. Besides that, what more is there?” He then confirmed that he is, indeed, over heels in love.

Who is Jon Hamm’s other half, then? Read on to learn every detail about Anna Osceola and her connection to the star.

Anna Osceola Was Born In Massachusetts

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

Anna OsceolaSource: People

Anna Osceola Is An Actress

In 2007, Osceola made her acting debut as Charlie in the TV movie Not Another High School Show. She had a three-episode storyline on Greek, and she also had roles on Rizzoli & Isles, NCIS, Law & Order: Special Victims Unit, and Law & Order: True Crime over the course of her career.

They Became Friends While Working On The Set Of “Mad Men”

After she appeared in the series finale of Man Men, where Hamm played a brief role, rumors began to circulate that he had met Osceola on-site. Osceola was cast as the kind front desk clerk at Don Draper’s (Hamm) spiritual California retreat, Esalen.

Hamm And Anna Osceola Became Friends While Working On The Set Of “Mad Men”

In 2020, Hamm and Osceola were initially romantically linked after they were seen together on multiple occasions. The two have been spotted together at restaurants, on the tennis court, and at the beach in the time since. In September of 2021, the couple was spotted enjoying a trip to Italy together, where they reportedly spent time on the water’s edge.

Hamm And Anna Osceola Appear Together In Hamm’s New Movie Confess

In the third film in the Fletch series, Hamm and Anna Osceola shared the screen once more. Hamm takes up Chevy Chase’s role as the semi-retired journalist Irwin M. Fletcher in the 1985 film Fletch and the 1989 film Fletch Lives.

Hamm’s character in the film is mixed up in a case of art theft in 2022. In addition, Osceola is featured in the project as the character “Larry.”

Hamm And Anna Osceola Both Stay Off Social Media

Hamm and Anna Osceola are both dependent on their respective social media platforms. Both members of the marriage prefer to keep their personal lives, including their romantic connections, out of the spotlight.

As Hamm explained to InStyle in 2017: “The idea of life is not to put dog ears on yourself and broadcast it online for everyone to see,” he has been outspoken about his decision to establish limits in the profession while maintaining his own identity.

He said, “It’s entertaining, it’s adorable, but it’s the visual equivalent of masturbating; there’s no reason other than quick enjoyment.”

Hamm And Anna Osceola Made Their Red Carpet Debut In March 2022

Hamm and Osceola’s romance took a major step forward in March 2022 when they attended their first red carpet event together at an Oscars afterparty. After making an appearance at the Vanity Fair Oscars afterparty, the couple headed to the annual Mercedes-Benz viewing party.

YouTube video

They have made other public appearances together since then, such as at the 2022 ESPY Awards in July and a screening of Confess, Fletch in September, and on the red carpet for the Sarah Silverman comedy Bedwetter in New York City in May.

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