Anna Osceola: 5 Things To Know About Actress, 32, Who Is Reportedly Dating Jon Hamm, 49

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Anna Osceola is the new woman in Jon Hamm‘s life! Five years after she appeared on the series finale of the Emmy-winning AMC show, Mad Men, which Jon led for its seven-season run, a new report suggests that the two co-stars have grown to be so much more. They were recently spotted playing a game of tennis in Los Feliz, CA in May, but their romance could go back even further! Here are five things to know about Anna Osceola.

1) Anna has a number of impressive credits to her name. The actress has mostly appeared on the small screen and got her first big break in 2007 playing Charlie in the TV movie Not Another High School Show. Between 2008-2009, she appeared in a number of episodes of the ABC Family series Greek as Robin Wylie. Most recently, Anna played Noelle Terlesky in the TV mini-series Law & Order True Crime in 2017. She has not acted since the mini-series.

2) She met Jon Hamm on the series finale of Mad Men. Anna played Clementine, a receptionist at the retreat Jon’s character Don Draper attends in the series finale. Although Anna was only featured limitedly in the final episode, she certainly made an impression on viewers and her cast members alike!

3) Anna and Jon have been seen together before. Anna and Jon’s first meeting goes back to 2015 on the show, but the two were spotted hanging out two years later in 2017. Prior to their recent tennis session this past May, the two were spotted getting some coffee in 2017. As quarantining for many across the country took full effect in March 2020, the two were spotted again picking up some food, according to Extra.

4) Anna isn’t Jon’s first famous romantic partner. Prior to getting together with Anna, Jon was in a longtime relationship with Jennifer Westfeldt from 1997-2015. Jon previously spoke in interviews about the depth of their relationship, but by 2015, their romance had run its course. A few years later, in 2019, Jon was seen spotted in New York City with Lindsay Shookus, who was previously linked to Ben Affleck. They attended a Broadway show together as well as an after party for Saturday Night Live.

5) Anna is originally from Cambridge, MA. Before setting off to Hollywood to pursue acting, she was born and raised in Cambridge, MA.