Who Is Jon Hamm’s Girlfriend, Anna Osceola? Relationship Info

Jon Hamm, the talented American actor, has made a name for himself in Hollywood over the years, thanks to his outstanding performances in several films and television shows.

The actor is most famous for portraying Don Draper in the television series Mad Men, which aired from 2007 to 2015. He was recognized for his performance with several awards, including a Golden Globe for Best Actor in a Drama Series, two Screen Actors Guild Awards for Outstanding Ensemble in a Drama Series, and a Primetime Emmy for Outstanding Lead Actor in a Drama Series. In total, he received 16 Emmy nominations for his work on Mad Men, as well as for his guest appearances on 30 Rock and Unbreakable Kimmy Schmidt.

Despite his success, he has kept his personal life private, but recently, he made headlines when he announced his engagement to actress Anna Osceola. In this article, we will dive deeper into their relationship and who Anna Osceola is.

Hamm And Osceola Met On Mad Men’s Set

Hamm and Osceola reportedly met on the set of Mad Men in 2015 when 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. However, it wasn’t until 2020 that they sparked romance rumors after being photographed together on several occasions.

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Who Is Jon Hamm’s Fiancee, Anna Osceola?

Anna Osceola was born in Cambridge, Massachusetts, on April 8, 1988. She grew up there before moving to California to become an actress. She started acting for the first time in 2007 when she played Charlie in the TV movie Not Another High School Show. During her career, she has been on many popular TV shows. She had a three-episode arc on Greek, and she has had roles on Rizzoli & Isles, NCIS, Law & Order: Special Victims Unit, and Law & Order True Crime.

Anna Osceola’s Relationship With Jon Hamm

Since Hamm and Osceola were first linked romantically in 2020, the couple has been photographed stepping out for meals, playing tennis, and enjoying a day at the beach. In September 2021, they even made a trip to Italy together, where they were photographed taking it easy on the water.

People confirmed in February 2023 that Hamm and Osceola were engaged. The next month, when she and Hamm went to the Vanity Fair Oscar afterparty, Osceola showed off her engagement ring, which has a single emerald-cut diamond.

In rare fashion, Hamm opened up about his relationship with Osceola during an interview with Howard Stern on his SiriusXM show in September 2022. He revealed that he’s been working on himself and his mental health with a therapist over the last couple of years, which has made their relationship even more meaningful. Hamm also confirmed that he is “very much so” in love with Osceola.

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Who Was Jon Hamm’s Previous Girlfriend?

Before he dated Osceola, Hamm was with Jennifer Westfeldt for a long time. But in 2015, after 18 years together, they broke up. After he broke up with Westfeldt, Hamm was seen with Jenny Slate in June 2017. At the time, sources said that they were only “friends.” In September 2019, Hamm went to the Broadway debut of Derren Brown: Secret with Lindsay Shookus, who used to work on Saturday Night Live.