Who is Anna Osceola? All Bout Jon Hamm's Fiancée

Jon Hamm Confirms Relationship with Younger Actress

After two years of dating, Jon Hamm has reportedly proposed to his girlfriend, actress Anna Osceola. The couple co-starred in the film Confess, Fletch. Hamm is best known for his role in Mad Men and more recently in Top Gun: Maverick.

Keeping Their Relationship Private

Hamm and Osceola have managed to keep their relationship private by not having a social media presence. Hamm has been vocal about his distaste for social media, stating that it is the “visual equivalent of masturbating” and lacks any real purpose other than immediate gratification.

Head Over Heels in Love

In a September 2022 interview with Howard Stern, Hamm expressed his love for Osceola, stating that he is “very much” in love with her. Hamm also revealed that he had to work through some emotional trauma, including the loss of his mother at a young age, in order to be open to the idea of settling down. Who is Anna Osceola? All Bout Jon Hamm’s Fiancée

Working on Himself and his Mental Health

Hamm credited therapy and working on his mental health as crucial in opening up the possibility of marriage and starting a family. He explained that losing his mother at a young age had created a wound that had blocked his emotional accessibility and vulnerability. However, after taking the time to unpack that trauma, Hamm was able to redefine his idea of happiness, life, and wellness.

Who is Anna Osceola? All Bout Jon Hamm’s Fiancée

The pair co-starred in Confess, Fletch. Prior to that, the sentient Ken Doll starred in Mad Men as the infamous yet mysterious Don Draper and most recently graced the big screen in Top Gun: Maverick as Beau “Cyclone” Simpson, the current head of the Top Gun flight school and a skeptic of Tom Cruise’s Pete “Maverick” Mitchell. While Hamm’s onscreen romantic heroes and leading men have their own cocky swagger, his personal life is much more low-key. Who is Anna Osceola? All Bout Jon Hamm’s Fiancée

It’s hard to keep relationships hush-hush in Hollywood, but Hamm and Osceola have done just that by not having a social media presence and keeping their relationship private. “The point of life is not to put dog ears on yourself and post it online for everyone to see,” he says. “It’s fun, it’s adorable, but it’s the visual equivalent of masturbating—there’s no point other than immediate gratification,” he told InStyle about being in a social media-free zone.

That said, Hamm is head over heels. In a September 2022 interview, he told Howard Stern that he “very much” is in love with Osceola.

“I’m in a relationship right now and … it’s comfortable, it’s a feeling of taking care of someone else and being taken care of,” he said. Hamm explained that being open to the idea of potentially settling down took work, especially coming to terms with losing his mother when he was 10 years old. Who is Anna Osceola? All Bout Jon Hamm’s Fiancée

“It’s also been a process of working on myself, my mental health, all the stuff with my therapist. 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,” Hamm said. “That blocks a lot of that availability and vulnerability.”

“It’s only been in the last couple of years, me kind of sitting down and 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,” he added. “It sounds hokey and whatever, but it’s real and it’s—for want of a better word—it’s what I’m working for.” Who is Anna Osceola? All Bout Jon Hamm’s Fiancée

Who is Jon Hamm’s fiancée?

Anna Osceola, a 35-year-old actress hailing from Cambridge, Massachusetts, has been in a relationship with Jon Hamm since 2020, despite their 17-year age difference. Osceola boasts a diverse range of acting credits, having landed her breakthrough role in the television film, Not Another High School Show, in 2007. She has also appeared in popular TV shows such as Greek, Rizzoli & Isles, and Law & Order: True Crime, and had a part in The Menendez Murders.

Where did Jon Hamm and Anna Osceola meet?

PEOPLE reported that the couple first crossed paths in 2015 while working on the set of Mad Men. Osceola portrayed a receptionist at the retreat where Hamm’s character, Don Draper, attended in the show’s finale. However, their romantic connection didn’t materialize until several years later. Despite being spotted together on a few occasions, the couple has largely kept their relationship private. They have been seen engaging in various activities such as spending time together on Super Bowl Sunday and vacationing in Italy in September 2021. Recently, the two were seen at the annual Mercedes-Benz party, which Hamm represents as an ambassador. This public appearance confirmed their relationship to the world. Who is Anna Osceola? All Bout Jon Hamm’s Fiancée

Osceola played the receptionist at the retreat that Hamm’s character Don Draper attended in the series finale. However, they didn’t connect romantically until years later. Since then, their relationship has been mostly private with a few outings being photographed. From Super Bowl Sunday activities together and enjoying an Italian vacation in September 2021, the pair have been spotted enjoying quality time with each other. Who is Anna Osceola? All Bout Jon Hamm’s Fiancée

The two attended the annual Mercedes-Benz party, the brand for which Hamm is an ambassador. This marked the couple’s first public outing together and served as confirmation they are in fact in a relationship.

Who did Jon Hamm date prior to Anna Osceola?

Before dating Anna Osceola, Jon Hamm was in a relationship with actress Jennifer Westfeldt for 18 years, starting from 1997 until their split in 2015. They released a joint statement at the time, expressing their intention to support each other moving forward. During their relationship, they collaborated on the 2011 film Friends with Kids and produced the Netflix limited series A Young Doctor’s Notebook.

Hamm went through rehab for alcohol abuse before the breakup, and he acknowledged Westfeldt’s support during his recovery. Prior to being with Osceola, Hamm was linked romantically to several women. In 2017, he was rumored to be dating his Aardvark co-star Jenny Slate after they were seen holding hands while leaving a movie theater. That same year, there were also rumors of him dating actress Dakota Johnson.