The actor previously dated Jennifer Westfeldt for 18 years
Jon Hamm and Anna Osceola Step Out Together in Los Angeles
Jon Hamm and Anna Osceola
| Credit: The Image Direct

Five years after Mad Men closed the curtain, the series may have spawned a real-life romance.

Jon Hamm and Anna Osceola, his one-time costar on the hit AMC drama, have been photographed together several times recently; Us Weekly reports that they are dating.

Hamm's rep has not commented. Osceola's manager did not immediately return PEOPLE's request for comment.

Hamm, 49, and Osceola, 32, were first spotted leaving a coffee shop together in 2017, according to Extra. In 2020, they've been photographed on a number of outings, including in February, when they stepped out for breakfast in Los Angeles.

In May, amid the coronavirus pandemic, they were seen picking up dinner to-go in the Los Feliz neighborhood of L.A. Hamm was spotted waiting in the car as Osceola retrieved the food. They were also seen playing tennis together in photos obtained by the Daily Mail.

Jon Hamm and Anna Osceola spotted picking up dinner to-go in LA

In the May 2015 series finale of Mad Men, "Person to Person," Osceola played the receptionist at the spiritual retreat where Don Draper (Hamm) ended up.

Last September, Hamm and producer Lindsay Shookus sparked dating rumors when they were spotted together at a Broadway play. A source close to Shookus, who previously dated Ben Affleck, told PEOPLE at the time that she and Hamm "have been friends for over a decade."

Hamm split from longtime girlfriend Jennifer Westfeldt in 2015 after 18 years together. In a 2017 interview with InStyle, Hamm acknowledged that being single "after being together for a long time" was "really hard."

"It sucks," he added.