Jon Hamm and Girlfriend Anna Osceola Make Red Carpet Debut at Oscars Viewing Party

Jon Hamm and Anna Osceola
Jon Hamm and Anna Osceola

Timothy Norris/FilmMagic

Jon Hamm is taking his relationship to the next level.

The Mad Men star made his red carpet debut with girlfriend Anna Osceola at an Oscars afterparty on Sunday night. The two attended an annual viewing party hosted by Mercedes-Benz, where Hamm is an ambassador. This marked the couple's first public outing together after nearly two years of dating.

The couple is believed to have met in 2015 when Osceola appeared on the final episode of Mad Men, playing the receptionist at the spiritual retreat where Don Draper (Hamm) ended up.

While Hamm and Osceola have largely kept their relationship private, word of their romance first spread in June 2020. They were seen leaving a coffee shop together in 2017, along with a number of outings from the last year, including picking up dinner and playing tennis together.

They were most recently seen enjoying their time together while on an Italian vacation in September 2021. The two were photographed on a boat near Arco dell'Elefante in Pantelleria.

Jon Hamm
Jon Hamm


Prior to his relationship with Osceola, Hamm was in a long-term relationship with actress Jennifer Westfeldt. In 2015, PEOPLE broke the news of the pair's split after 18 years together.

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"We will continue to be supportive of each other in every way possible moving forward," they said in a joint statement.

RELATED: Jon Hamm and Anna Osceola Enjoy Fun Day of Swimming and Snorkeling While Vacationing in Italy

And while Hamm wasn't up for any awards on Sunday night, he does have a few films in the works. He's finished filming Top Gun: Maverick — where he'll play Cyclone — as well as a film called Coroner's Office.

Of Cyclone, Hamm told Men's Journal that the character is "not so much of a father figure, the way Viper was to Tom," he said.

"He's air boss of the fighter wing," he says. "He has a lot of authority and responsibility. When that rubs up against Maverick, there's friction, as you would guess. I provide the friction."