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Jon Hamm Plays Tennis with Anna Osceola, His Longtime Rumored Girlfriend

Jon Hamm heads to the tennis courts with Anna Osceola to play a game of one-on-one on Friday afternoon (May 22) in Los Feliz, Calif.

The 49-year-old actor has been spotted with Anna, 32, many times over the past three years though they’ve kept their relationship under wraps this whole time. After their friendly game of tennis, they were seen sharing a cute handshake.

Fans have been talking about Jon and Anna being a possible couple for quite some time and now it seems likely that they’re quarantining together. The two actors were also seen getting takeout food together on March 21.

Anna is an actress who guest starred on the series finale of Jon‘s show Mad Men. She played the role of Clementine and had a scene alongside Jon. Most recently, she was seen on the limited series Law & Order True Crime.

The first photos we have of Jon and Anna together date all the way back to January 2017, when they were spotted together at the gym. They were also spotted together at the tennis courts in March 2018. Reddit users spotted the pair at a basketball game in June 2019.

75+ pictures inside of Jon Hamm playing tennis with Anna OsceolaMore Here! »

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Jon Hamm Plays Tennis With Anna Osceola

Jon Hamm holds onto some balls while at a tennis court with Mad Men actress Anna Osceola on Tuesday morning (March 27) in Los Angeles.

The 47-year-old Emmy-winning actor and his friend played a round of tennis together and then left in the same car.

PHOTOS: Check out the latest pics of Jon Hamm

Jon split from longtime partner Jennifer Westfeldt in 2015 and while he has been linked to several actresses in a slew of rumors over the past two years, nothing has been confirmed.

30+ pictures inside of Jon Hamm playing tennis… More Here! »

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Jon Hamm Steps Out in Sweats with Anna Osceola

Jon Hamm holds his iced beverage while leaving a coffee shop on Friday morning (January 27) in Los Feliz, Calif.

The 45-year-old former Mad Men actor stepped out in his sweats with fellow Mad Men star Anna Osceola and it looks like they had just come from a workout.

PHOTOS: Check out the latest pics of Jon Hamm

Jon and his longtime partner Jennifer Westfelt split back in September 2015 after 18 years together and he has not yet been linked to anyone new.

Earlier this week, Jon revealed where he thinks his Mad Men character Don Draper would be today.

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