Who did Anna Osceola play on Mad Men? Character explored amid Jon Hamm engagement report

American actor Jon Hamm and actress Anna Osceola are reportedly engaged to be married.

The news was confirmed by People Magazine on Monday, February 27, 2023, although an official announcement is yet to come from either of the stars.

Hamm and Osceola have been dating for two years but kept most of their relationship under wraps, and were only photographed together at red-carpet events.

Jon Hamm and Anna Osceola. (Photo via Getty Images)

Jon Hamm and Anna Osceola reportedly first crossed each other's paths in 2015 while shooting for AMC's drama series, Mad Men.

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Anna Osceola had a small role alongside Jon Hamm in Mad Men

Anna Osceola appeared in the final episode of Mad Men in a small role as Clementine, a receptionist at a spiritual retreat that Jon Hamm's character attended. At the time of filming, Hamm was in a relationship with Jennifer Westfeldt. However, the couple separated months later, after spending 18 years together.

After the series ended, Hamm and Osceola reportedly stayed in touch and were also spotted buying coffee in 2017. Rumors about their romantic relationship began swirling in May 2020, when they were seen hanging out on the beach and playing tennis together.

Some media outlets also reported that Jon Hamm and Anna quarantined together. In March 2022, the duo made an appearance on the red carpet at the Vanity Fair Oscars party.

In September 2022, Hamm appeared on an episode of Howard Stern's show, SiriusXM, where he opened up about the possibility of getting married.

The Baby Driver star called his relationship "comfortable." He added:

"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."

He said that it has opened up the possibility of being married and having kids and even defining a new version of happiness, life, and wellness for him. While stating that it might sound "hokey and whatever," the actor said that it was real for him and it was something he was working on.

Before being with 34-year-old Osceola, Hamm was involved in a long-term relationship with Jennifer Westfeldt. The duo split up amicably, but some reports suggest things got sour between the two due of Jon's substance issues and frequent partying.

Anna Osceola is a native of Massachusetts, as per People Magazine. She later moved to California to pursue an acting career.

As per her IMDb profile, her acting credits include Not Another High School Show, Conspiracy, Saving Grace, Greek, and An American Carol. She was also a part of Rizzoli & Isles, NCIS, Guy Suave: Homicidal Spy, Law & Order: Special Victims Unit, and Law & Order True Crime, among others.