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

A big night to take a big step (and repeat).
 
Almost two years after they first began sparking romance rumors, Mad Men alum Jon Hamm and girlfriend Anna Osceola made their red carpet debut at an after party for the 2022 Academy Awards. The couple attended an annual viewing party hosted by Mercedes-Benz—Jon is a brand ambassador—in Beverly Hills on Sunday, March 27.
 
Having reportedly first met while filming the Mad Men series finale in 2015,a source confirmed to Us Weekly in June 2020 that the actors, were indeed, an item—Jon’s first serious romance after announcing the end of his nearly two-decade relationship with screenwriter Jennifer Westfeldt in 2015.
 
“With great sadness, we have decided to separate, after 18 years of love and shared history,” read a joint statement released from the pair at the time. “We will continue to be supportive of each other in every way possible moving forward.”