Is Jon Hamm Dating His Former Mad Men Costar Anna Osceola?

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.

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