Jon Hamm Anna Osceola Don Draper show stars reports Jon Hamm Anna Osceola Don Draper

Jon Hamm, 49, Dating ‘Mad Men’ Guest Star Anna Osceola, 32, 5 Years After Finale

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Jon Hamm reportedly has a new woman in his life! The 49-year-old actor is dating Anna Osceola, 32, according to Us Weekly.

The mag’s confirmation of this hot new romance comes after the stars were photographed playing tennis together in May. Anna was a guest star on the season finale of Mad Men in 2015, so she briefly shared the screen with Jon on the hit AMC show.

In the Mad Men finale, Anna played the receptionist at a retreat that Jon’s character, Don Draper, visited. In real life, Jon and Anna have actually been spotted together several times amidst the coronavirus.

A few eagle-eyed fans have even been speculating that there was something going on between them since March! Actually, this connection could potentially even date back to

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